Synthesis of nonracemic 2,3,6-trisubstituted piperidine derivatives from sugar lactones via tandem Wittig [2+3] cycloaddition reaction. A novel entry to prosopis and Cassia alkaloids

Tetrahedron

Volumn 55, Issue 4, 1999, Pages 1043-1056

  Herdeis, Claus ^a   Schiffer, Thomas ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; PIPERIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

CASSIA; PROSOPIS;

EID: 0033593268     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01085-0     Document Type: Article

References (61)

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2. Gross, D. Prog. Chem. Org. Nat. Prod. 1971, 29, 1-59. Strunz, G. M.; Findlay, J. A. The Alkaloids, Ed. Brossi, A. Acad. Press. 1985, 29, 89-174. Highet, R. J. J. Org. Chem. 1964,29, 471-474. Coke, J. L.; Rice, W. J. J. Org. Chem. 1966, 31, 1010-1012. Jewers, K. Nagler, M. J.; Zirvi, K. A.; Amir, F. Phytochemistry 1976, 15, 238-240. Christofidis, I.; Welter, A.; Jadot, J. Tetrahedron 1977, 33, 977-979. Aguinaldo, A. M.; Reed, R. W. Phytochemistry 1990, 29, 2309-2313. Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672.
3. Gross, D. Prog. Chem. Org. Nat. Prod. 1971, 29, 1-59. Strunz, G. M.; Findlay, J. A. The Alkaloids, Ed. Brossi, A. Acad. Press. 1985, 29, 89-174. Highet, R. J. J. Org. Chem. 1964,29, 471-474. Coke, J. L.; Rice, W. J. J. Org. Chem. 1966, 31, 1010-1012. Jewers, K. Nagler, M. J.; Zirvi, K. A.; Amir, F. Phytochemistry 1976, 15, 238-240. Christofidis, I.; Welter, A.; Jadot, J. Tetrahedron 1977, 33, 977-979. Aguinaldo, A. M.; Reed, R. W. Phytochemistry 1990, 29, 2309-2313. Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672.
4. Gross, D. Prog. Chem. Org. Nat. Prod. 1971, 29, 1-59. Strunz, G. M.; Findlay, J. A. The Alkaloids, Ed. Brossi, A. Acad. Press. 1985, 29, 89-174. Highet, R. J. J. Org. Chem. 1964,29, 471-474. Coke, J. L.; Rice, W. J. J. Org. Chem. 1966, 31, 1010-1012. Jewers, K. Nagler, M. J.; Zirvi, K. A.; Amir, F. Phytochemistry 1976, 15, 238-240. Christofidis, I.; Welter, A.; Jadot, J. Tetrahedron 1977, 33, 977-979. Aguinaldo, A. M.; Reed, R. W. Phytochemistry 1990, 29, 2309-2313. Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672.
5. Gross, D. Prog. Chem. Org. Nat. Prod. 1971, 29, 1-59. Strunz, G. M.; Findlay, J. A. The Alkaloids, Ed. Brossi, A. Acad. Press. 1985, 29, 89-174. Highet, R. J. J. Org. Chem. 1964,29, 471-474. Coke, J. L.; Rice, W. J. J. Org. Chem. 1966, 31, 1010-1012. Jewers, K. Nagler, M. J.; Zirvi, K. A.; Amir, F. Phytochemistry 1976, 15, 238-240. Christofidis, I.; Welter, A.; Jadot, J. Tetrahedron 1977, 33, 977-979. Aguinaldo, A. M.; Reed, R. W. Phytochemistry 1990, 29, 2309-2313. Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672.
6. Gross, D. Prog. Chem. Org. Nat. Prod. 1971, 29, 1-59. Strunz, G. M.; Findlay, J. A. The Alkaloids, Ed. Brossi, A. Acad. Press. 1985, 29, 89-174. Highet, R. J. J. Org. Chem. 1964,29, 471-474. Coke, J. L.; Rice, W. J. J. Org. Chem. 1966, 31, 1010-1012. Jewers, K. Nagler, M. J.; Zirvi, K. A.; Amir, F. Phytochemistry 1976, 15, 238-240. Christofidis, I.; Welter, A.; Jadot, J. Tetrahedron 1977, 33, 977-979. Aguinaldo, A. M.; Reed, R. W. Phytochemistry 1990, 29, 2309-2313. Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672.
7. Gross, D. Prog. Chem. Org. Nat. Prod. 1971, 29, 1-59. Strunz, G. M.; Findlay, J. A. The Alkaloids, Ed. Brossi, A. Acad. Press. 1985, 29, 89-174. Highet, R. J. J. Org. Chem. 1964,29, 471-474. Coke, J. L.; Rice, W. J. J. Org. Chem. 1966, 31, 1010-1012. Jewers, K. Nagler, M. J.; Zirvi, K. A.; Amir, F. Phytochemistry 1976, 15, 238-240. Christofidis, I.; Welter, A.; Jadot, J. Tetrahedron 1977, 33, 977-979. Aguinaldo, A. M.; Reed, R. W. Phytochemistry 1990, 29, 2309-2313. Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672.
8. Gross, D. Prog. Chem. Org. Nat. Prod. 1971, 29, 1-59. Strunz, G. M.; Findlay, J. A. The Alkaloids, Ed. Brossi, A. Acad. Press. 1985, 29, 89-174. Highet, R. J. J. Org. Chem. 1964,29, 471-474. Coke, J. L.; Rice, W. J. J. Org. Chem. 1966, 31, 1010-1012. Jewers, K. Nagler, M. J.; Zirvi, K. A.; Amir, F. Phytochemistry 1976, 15, 238-240. Christofidis, I.; Welter, A.; Jadot, J. Tetrahedron 1977, 33, 977-979. Aguinaldo, A. M.; Reed, R. W. Phytochemistry 1990, 29, 2309-2313. Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672.
9. Gross, D. Prog. Chem. Org. Nat. Prod. 1971, 29, 1-59. Strunz, G. M.; Findlay, J. A. The Alkaloids, Ed. Brossi, A. Acad. Press. 1985, 29, 89-174. Highet, R. J. J. Org. Chem. 1964,29, 471-474. Coke, J. L.; Rice, W. J. J. Org. Chem. 1966, 31, 1010-1012. Jewers, K. Nagler, M. J.; Zirvi, K. A.; Amir, F. Phytochemistry 1976, 15, 238-240. Christofidis, I.; Welter, A.; Jadot, J. Tetrahedron 1977, 33, 977-979. Aguinaldo, A. M.; Reed, R. W. Phytochemistry 1990, 29, 2309-2313. Hasseberg, H.-A.; Gerlach, H. Liebigs Ann. Chem. 1989, 255-261. Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669-1672.
10. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
11. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
12. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
13. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
14. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
15. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
16. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
17. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
18. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
19. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
20. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
21. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
22. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
23. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
24. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
25. Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 36, 3391-3394. Ciufolini, M. A.; Hermann, C. W.;Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473-3475. Lu, Z.-H.; Zhou, W.-S. Tetrahedron 1993, 49, 4659-4664. Momose, T.; Toyooka, N. Tetrahedron Lett. 1993, 34, 5785-5786. Takao, K.; Nigawara, Y.; Nishino, E.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704. Toyooka, N.; Yoshida, Y.; Momose, T. Tetrahedron Lett. 1995, 36, 3715-3718. Momose, T.; Toyooka, N. Heterocycles, 1995, 40, 137-138. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc. Perkin Trans. 1, 1996, 793-802. Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482. Momose, T.; Toyooka, N.; Jin, M. J. Chem. Soc. Perkin Trans. 1 1997, 2005-2013. Oetting, J. Holzkamp, J. Meyer, H. H.; Pahl, A. Tetrahedron: Asymmetry 1997, 8, 477-484. Pahl, A.; Oetting, J.; Holzkamp, J.; Meyer, H. H. Tetrahedron 1997, 53, 7255-7266. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron, 1997, 53, 9553-9574. Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry, 1997, 8, 3887-3893. Enders, D.; Bartzen, D. Liebigs Ann./Recueil 1997, 1115-1123. Sánchez-Sancho, F.; Herradón, B. Tetrahedron: Asymmetry, 1998, 9, 1951-1965. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron, 1998, 54, 8783-8796. Pahl, A.; Wartchow, R.; Meyer, H. H. Tetrahedron Lett. 1998, 39, 2095-2096.
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29. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
30. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
31. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
32. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
33. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
34. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
35. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
36. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
37. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
38. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
39. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
40. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
41. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
42. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
43. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
44. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
45. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
46. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
47. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
48. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
49. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
50. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
51. Azide-olefin cycloaddition in general: Huisgen, R. Angew. Chem. 1963, 75, 602-637. Huisgen, R. J. Org. Chem. 1976, 41, 403-419. Lwowski, W. in "1,3-Dipolar Cycloaddition Chemistry", Ed. Padwa, A. John Wiley, New York, 1984, Vol. 1, 559-651. Hassner, A.; Amarasekara, A. S.; Andisik, D. J. Org. Chem. 1988, 53, 27-30. Schultz, A. G. Adv. Cycloadd. 1988, 1, 53-85. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. In natural product syntheses: Logothetis, A. L. J. Am. Chem. Soc. 1965, 87, 749-754. Schultz, A. G.; Ravichandran, R. J. Org. Chem. 1980, 45, 5009-5011. Schultz, A. G.; Sha, C.-K. J. Org. Chem. 1980, 45, 2040-2041. Kozikowski, A. P.; Greco, M. N. Tetrahedron Lett. 1982, 23, 2005-2008. Mulzer, J. Nachr. Chem. Tech. 1984, 32, 882-887, and 961-965. Buchanan, J. G.; Edgar, A. R.; Hewitt, B. D. J. Chem. Soc., Perkin Trans. 1, 1987, 2371-2376. Bennett III, R. B.; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990, 55, 5719-5738. Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683-4687. Bernet, B.; Bulusu Murty, A. R. C.; Vasella, A. Helv. Chim. Acta 1990, 73, 940-958. Kim, N.-S; Kang, C. H.; Cha, J. K. Tetrahedron Lett. 1994, 35, 3489-3492. Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757-5762. Taber, D. F.; Rahimizadeh, M.; You, K. K. J. Org. Chem. 1995, 60, 529-531. Wild, R.; Schmidt, R, R. Liebigs Ann.chem. 1995, 755-764. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron 1996, 52, 3107-3116. Krülle, T.M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807-3820. Molander, G.A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347-4350.
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56. Triazoline-diazoamine equlibrium depends on the piperidine ring substitutents. Highly substituted derivatives provide only diazoamines; see: Herdeis, C.; Schiffer, T. Tetrahedron, 1996, 52, 14745-14756. see also: Hoye, T. R.; Deerfield, D. W. in 1,3 Dipolar Cycloaddition Chemistry, 1984, Ed. Padwa, A. Vol.2, p. 317, J. Wiley & Sons, Inc.
57. Triazoline-diazoamine equlibrium depends on the piperidine ring substitutents. Highly substituted derivatives provide only diazoamines; see: Herdeis, C.; Schiffer, T. Tetrahedron, 1996, 52, 14745-14756. see also: Hoye, T. R.; Deerfield, D. W. in 1,3 Dipolar Cycloaddition Chemistry, 1984, Ed. Padwa, A. Vol.2, p. 317, J. Wiley & Sons, Inc.
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