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Volumn 63, Issue 15, 1998, Pages 5031-5041

A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2-Butynoates and Dimethyl Acetylenedicarboxylate with Imines: A Convenient Synthesis of Pentabromopseudilin

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EID: 0000182934     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9723063     Document Type: Article
Times cited : (343)

References (78)
  • 2
    • 0029945669 scopus 로고    scopus 로고
    • For recent examples, see: (a) Winn, M.; von Geldern, T. W.; Opgenorth, T. J.; Jae, H.-S.; Tasker, A. S.; Boyd, S. A.; Kester, J. A.; Mantei, R. A.; Bal, R.; Sorensen, B. K.; Wu-Wong, J. R.; Chion, W. J.; Dixon, D. B.; Novosad, E. I.; Hernandez, L.; Marsh, K. C. J. Med. Chem. 1996, 39, 1039. (b) Wittenberger, S. J. J. Org. Chem. 1996, 61, 356. (c) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. (d) Yoda, Y.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (e) Kang, S. H.; Choi, H. Chem. Commun. 1996, 1521. (f) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531. (g) Shibano, M.; Kitagawa, S.; Kusano, G. Chem. Pharm. Bull. 1997, 45, 505. (h) Miyata, O.; Ozawa, Y.; Nimomiya, I.; Naito, T. Synlett 1997, 275. (i) Bachi, M. D.; Melman, A. J. Org. Chem. 1997, 62, 1896.
    • (1996) J. Med. Chem. , vol.39 , pp. 1039
    • Winn, M.1    Von Geldern, T.W.2    Opgenorth, T.J.3    Jae, H.-S.4    Tasker, A.S.5    Boyd, S.A.6    Kester, J.A.7    Mantei, R.A.8    Bal, R.9    Sorensen, B.K.10    Wu-Wong, J.R.11    Chion, W.J.12    Dixon, D.B.13    Novosad, E.I.14    Hernandez, L.15    Marsh, K.C.16
  • 3
    • 0030069174 scopus 로고    scopus 로고
    • For recent examples, see: (a) Winn, M.; von Geldern, T. W.; Opgenorth, T. J.; Jae, H.-S.; Tasker, A. S.; Boyd, S. A.; Kester, J. A.; Mantei, R. A.; Bal, R.; Sorensen, B. K.; Wu-Wong, J. R.; Chion, W. J.; Dixon, D. B.; Novosad, E. I.; Hernandez, L.; Marsh, K. C. J. Med. Chem. 1996, 39, 1039. (b) Wittenberger, S. J. J. Org. Chem. 1996, 61, 356. (c) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. (d) Yoda, Y.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (e) Kang, S. H.; Choi, H. Chem. Commun. 1996, 1521. (f) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531. (g) Shibano, M.; Kitagawa, S.; Kusano, G. Chem. Pharm. Bull. 1997, 45, 505. (h) Miyata, O.; Ozawa, Y.; Nimomiya, I.; Naito, T. Synlett 1997, 275. (i) Bachi, M. D.; Melman, A. J. Org. Chem. 1997, 62, 1896.
    • (1996) J. Org. Chem. , vol.61 , pp. 356
    • Wittenberger, S.J.1
  • 4
    • 0030047131 scopus 로고    scopus 로고
    • For recent examples, see: (a) Winn, M.; von Geldern, T. W.; Opgenorth, T. J.; Jae, H.-S.; Tasker, A. S.; Boyd, S. A.; Kester, J. A.; Mantei, R. A.; Bal, R.; Sorensen, B. K.; Wu-Wong, J. R.; Chion, W. J.; Dixon, D. B.; Novosad, E. I.; Hernandez, L.; Marsh, K. C. J. Med. Chem. 1996, 39, 1039. (b) Wittenberger, S. J. J. Org. Chem. 1996, 61, 356. (c) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. (d) Yoda, Y.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (e) Kang, S. H.; Choi, H. Chem. Commun. 1996, 1521. (f) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531. (g) Shibano, M.; Kitagawa, S.; Kusano, G. Chem. Pharm. Bull. 1997, 45, 505. (h) Miyata, O.; Ozawa, Y.; Nimomiya, I.; Naito, T. Synlett 1997, 275. (i) Bachi, M. D.; Melman, A. J. Org. Chem. 1997, 62, 1896.
    • (1996) J. Org. Chem. , vol.61 , pp. 566
    • Mulzer, J.1    Meier, A.2    Buschmann, J.3    Luger, P.4
  • 5
    • 0030020611 scopus 로고    scopus 로고
    • For recent examples, see: (a) Winn, M.; von Geldern, T. W.; Opgenorth, T. J.; Jae, H.-S.; Tasker, A. S.; Boyd, S. A.; Kester, J. A.; Mantei, R. A.; Bal, R.; Sorensen, B. K.; Wu-Wong, J. R.; Chion, W. J.; Dixon, D. B.; Novosad, E. I.; Hernandez, L.; Marsh, K. C. J. Med. Chem. 1996, 39, 1039. (b) Wittenberger, S. J. J. Org. Chem. 1996, 61, 356. (c) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. (d) Yoda, Y.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (e) Kang, S. H.; Choi, H. Chem. Commun. 1996, 1521. (f) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531. (g) Shibano, M.; Kitagawa, S.; Kusano, G. Chem. Pharm. Bull. 1997, 45, 505. (h) Miyata, O.; Ozawa, Y.; Nimomiya, I.; Naito, T. Synlett 1997, 275. (i) Bachi, M. D.; Melman, A. J. Org. Chem. 1997, 62, 1896.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 373
    • Yoda, Y.1    Yamazaki, H.2    Takabe, K.3
  • 6
    • 0002895663 scopus 로고    scopus 로고
    • For recent examples, see: (a) Winn, M.; von Geldern, T. W.; Opgenorth, T. J.; Jae, H.-S.; Tasker, A. S.; Boyd, S. A.; Kester, J. A.; Mantei, R. A.; Bal, R.; Sorensen, B. K.; Wu-Wong, J. R.; Chion, W. J.; Dixon, D. B.; Novosad, E. I.; Hernandez, L.; Marsh, K. C. J. Med. Chem. 1996, 39, 1039. (b) Wittenberger, S. J. J. Org. Chem. 1996, 61, 356. (c) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. (d) Yoda, Y.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (e) Kang, S. H.; Choi, H. Chem. Commun. 1996, 1521. (f) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531. (g) Shibano, M.; Kitagawa, S.; Kusano, G. Chem. Pharm. Bull. 1997, 45, 505. (h) Miyata, O.; Ozawa, Y.; Nimomiya, I.; Naito, T. Synlett 1997, 275. (i) Bachi, M. D.; Melman, A. J. Org. Chem. 1997, 62, 1896.
    • (1996) Chem. Commun. , pp. 1521
    • Kang, S.H.1    Choi, H.2
  • 7
    • 0030605868 scopus 로고    scopus 로고
    • For recent examples, see: (a) Winn, M.; von Geldern, T. W.; Opgenorth, T. J.; Jae, H.-S.; Tasker, A. S.; Boyd, S. A.; Kester, J. A.; Mantei, R. A.; Bal, R.; Sorensen, B. K.; Wu-Wong, J. R.; Chion, W. J.; Dixon, D. B.; Novosad, E. I.; Hernandez, L.; Marsh, K. C. J. Med. Chem. 1996, 39, 1039. (b) Wittenberger, S. J. J. Org. Chem. 1996, 61, 356. (c) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. (d) Yoda, Y.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (e) Kang, S. H.; Choi, H. Chem. Commun. 1996, 1521. (f) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531. (g) Shibano, M.; Kitagawa, S.; Kusano, G. Chem. Pharm. Bull. 1997, 45, 505. (h) Miyata, O.; Ozawa, Y.; Nimomiya, I.; Naito, T. Synlett 1997, 275. (i) Bachi, M. D.; Melman, A. J. Org. Chem. 1997, 62, 1896.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5531
    • Yoda, H.1    Nakajima, T.2    Takabe, K.3
  • 8
    • 0030951738 scopus 로고    scopus 로고
    • For recent examples, see: (a) Winn, M.; von Geldern, T. W.; Opgenorth, T. J.; Jae, H.-S.; Tasker, A. S.; Boyd, S. A.; Kester, J. A.; Mantei, R. A.; Bal, R.; Sorensen, B. K.; Wu-Wong, J. R.; Chion, W. J.; Dixon, D. B.; Novosad, E. I.; Hernandez, L.; Marsh, K. C. J. Med. Chem. 1996, 39, 1039. (b) Wittenberger, S. J. J. Org. Chem. 1996, 61, 356. (c) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. (d) Yoda, Y.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (e) Kang, S. H.; Choi, H. Chem. Commun. 1996, 1521. (f) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531. (g) Shibano, M.; Kitagawa, S.; Kusano, G. Chem. Pharm. Bull. 1997, 45, 505. (h) Miyata, O.; Ozawa, Y.; Nimomiya, I.; Naito, T. Synlett 1997, 275. (i) Bachi, M. D.; Melman, A. J. Org. Chem. 1997, 62, 1896.
    • (1997) Chem. Pharm. Bull. , vol.45 , pp. 505
    • Shibano, M.1    Kitagawa, S.2    Kusano, G.3
  • 9
    • 0001688764 scopus 로고    scopus 로고
    • For recent examples, see: (a) Winn, M.; von Geldern, T. W.; Opgenorth, T. J.; Jae, H.-S.; Tasker, A. S.; Boyd, S. A.; Kester, J. A.; Mantei, R. A.; Bal, R.; Sorensen, B. K.; Wu-Wong, J. R.; Chion, W. J.; Dixon, D. B.; Novosad, E. I.; Hernandez, L.; Marsh, K. C. J. Med. Chem. 1996, 39, 1039. (b) Wittenberger, S. J. J. Org. Chem. 1996, 61, 356. (c) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. (d) Yoda, Y.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (e) Kang, S. H.; Choi, H. Chem. Commun. 1996, 1521. (f) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531. (g) Shibano, M.; Kitagawa, S.; Kusano, G. Chem. Pharm. Bull. 1997, 45, 505. (h) Miyata, O.; Ozawa, Y.; Nimomiya, I.; Naito, T. Synlett 1997, 275. (i) Bachi, M. D.; Melman, A. J. Org. Chem. 1997, 62, 1896.
    • (1997) Synlett , pp. 275
    • Miyata, O.1    Ozawa, Y.2    Nimomiya, I.3    Naito, T.4
  • 10
    • 0001164390 scopus 로고    scopus 로고
    • For recent examples, see: (a) Winn, M.; von Geldern, T. W.; Opgenorth, T. J.; Jae, H.-S.; Tasker, A. S.; Boyd, S. A.; Kester, J. A.; Mantei, R. A.; Bal, R.; Sorensen, B. K.; Wu-Wong, J. R.; Chion, W. J.; Dixon, D. B.; Novosad, E. I.; Hernandez, L.; Marsh, K. C. J. Med. Chem. 1996, 39, 1039. (b) Wittenberger, S. J. J. Org. Chem. 1996, 61, 356. (c) Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566. (d) Yoda, Y.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (e) Kang, S. H.; Choi, H. Chem. Commun. 1996, 1521. (f) Yoda, H.; Nakajima, T.; Takabe, K. Tetrahedron Lett. 1996, 37, 5531. (g) Shibano, M.; Kitagawa, S.; Kusano, G. Chem. Pharm. Bull. 1997, 45, 505. (h) Miyata, O.; Ozawa, Y.; Nimomiya, I.; Naito, T. Synlett 1997, 275. (i) Bachi, M. D.; Melman, A. J. Org. Chem. 1997, 62, 1896.
    • (1997) J. Org. Chem. , vol.62 , pp. 1896
    • Bachi, M.D.1    Melman, A.2
  • 11
    • 84943376011 scopus 로고
    • Katritzky and Rees Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon Press: Oxford
    • For a general review, see: Bird, C. W.; Cheeseman, G. W. H. In Katritzky and Rees Comprehensive Heterocyclic Chemistry; Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon Press: Oxford, 1984; Vol. 4, p 89.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 89
    • Bird, C.W.1    Cheeseman, G.W.H.2
  • 13
    • 0000002236 scopus 로고
    • Padwa, A., Ed.; Wiley-Interscience: New York, Chapter 6
    • For reviews on azomethine ylides, see: (a) Lown, J. W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984; Vol. 1, Chapter 6, p 653. (b) Tsuge, O.; Kanemasa, S. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, 1989; Vol. 45, p 231.
    • (1984) 1,3-Dipolar Cycloaddition Chemistry , vol.1 , pp. 653
    • Lown, J.W.1
  • 14
    • 8744290197 scopus 로고
    • Katritzky, A. R., Ed.; Academic Press: San Diego
    • For reviews on azomethine ylides, see: (a) Lown, J. W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984; Vol. 1, Chapter 6, p 653. (b) Tsuge, O.; Kanemasa, S. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, 1989; Vol. 45, p 231.
    • (1989) Advances in Heterocyclic Chemistry , vol.45 , pp. 231
    • Tsuge, O.1    Kanemasa, S.2
  • 15
    • 15044342910 scopus 로고
    • Katritzky, A. R., Ed.; Academic Press: San Diego
    • For a recent review on nitrogen radicals, see: Esker, J. L.; Newcomb, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, 1993; Vol. 58, p 1.
    • (1993) Advances in Heterocyclic Chemistry , vol.58 , pp. 1
    • Esker, J.L.1    Newcomb, M.2
  • 16
    • 0030590425 scopus 로고    scopus 로고
    • For recent examples, see: (a) Coldham, I.; Hufton, R. Tetrahe-dron 1996, 52, 12541. (b) Steiner, A.; Wessig, P.; Polborn, K. Helv. Chim. Acta 1996, 79, 1843. (c) Hollinshead, S. P. Tetrahedron Lett. 1996, 37, 9157. (d) Tokuda, M.; Fujita, H.; Nitta, M.; Suginome, H. Heterocycles 1996, 42, 385. (e) Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. (f) Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200. (g) Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. (i) Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895. (j) Alvarez-Ibarra, C.; Csaky, A. G.; Lopez de Silanes, I.; Quiroga, M. L. J. Org. Chem. 1997, 62, 479.
    • (1996) Tetrahedron , vol.52 , pp. 12541
    • Coldham, I.1    Hufton, R.2
  • 17
    • 0029912697 scopus 로고    scopus 로고
    • For recent examples, see: (a) Coldham, I.; Hufton, R. Tetrahe-dron 1996, 52, 12541. (b) Steiner, A.; Wessig, P.; Polborn, K. Helv. Chim. Acta 1996, 79, 1843. (c) Hollinshead, S. P. Tetrahedron Lett. 1996, 37, 9157. (d) Tokuda, M.; Fujita, H.; Nitta, M.; Suginome, H. Heterocycles 1996, 42, 385. (e) Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. (f) Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200. (g) Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. (i) Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895. (j) Alvarez-Ibarra, C.; Csaky, A. G.; Lopez de Silanes, I.; Quiroga, M. L. J. Org. Chem. 1997, 62, 479.
    • (1996) Helv. Chim. Acta , vol.79 , pp. 1843
    • Steiner, A.1    Wessig, P.2    Polborn, K.3
  • 18
    • 0030590979 scopus 로고    scopus 로고
    • For recent examples, see: (a) Coldham, I.; Hufton, R. Tetrahe-dron 1996, 52, 12541. (b) Steiner, A.; Wessig, P.; Polborn, K. Helv. Chim. Acta 1996, 79, 1843. (c) Hollinshead, S. P. Tetrahedron Lett. 1996, 37, 9157. (d) Tokuda, M.; Fujita, H.; Nitta, M.; Suginome, H. Heterocycles 1996, 42, 385. (e) Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. (f) Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200. (g) Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. (i) Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895. (j) Alvarez-Ibarra, C.; Csaky, A. G.; Lopez de Silanes, I.; Quiroga, M. L. J. Org. Chem. 1997, 62, 479.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 9157
    • Hollinshead, S.P.1
  • 19
    • 0242582164 scopus 로고    scopus 로고
    • For recent examples, see: (a) Coldham, I.; Hufton, R. Tetrahe-dron 1996, 52, 12541. (b) Steiner, A.; Wessig, P.; Polborn, K. Helv. Chim. Acta 1996, 79, 1843. (c) Hollinshead, S. P. Tetrahedron Lett. 1996, 37, 9157. (d) Tokuda, M.; Fujita, H.; Nitta, M.; Suginome, H. Heterocycles 1996, 42, 385. (e) Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. (f) Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200. (g) Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. (i) Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895. (j) Alvarez-Ibarra, C.; Csaky, A. G.; Lopez de Silanes, I.; Quiroga, M. L. J. Org. Chem. 1997, 62, 479.
    • (1996) Heterocycles , vol.42 , pp. 385
    • Tokuda, M.1    Fujita, H.2    Nitta, M.3    Suginome, H.4
  • 20
    • 0030071356 scopus 로고    scopus 로고
    • For recent examples, see: (a) Coldham, I.; Hufton, R. Tetrahe-dron 1996, 52, 12541. (b) Steiner, A.; Wessig, P.; Polborn, K. Helv. Chim. Acta 1996, 79, 1843. (c) Hollinshead, S. P. Tetrahedron Lett. 1996, 37, 9157. (d) Tokuda, M.; Fujita, H.; Nitta, M.; Suginome, H. Heterocycles 1996, 42, 385. (e) Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. (f) Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200. (g) Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. (i) Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895. (j) Alvarez-Ibarra, C.; Csaky, A. G.; Lopez de Silanes, I.; Quiroga, M. L. J. Org. Chem. 1997, 62, 479.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 715
    • Wu, S.1    Lee, S.2    Beak, P.3
  • 21
    • 0029886698 scopus 로고    scopus 로고
    • For recent examples, see: (a) Coldham, I.; Hufton, R. Tetrahe-dron 1996, 52, 12541. (b) Steiner, A.; Wessig, P.; Polborn, K. Helv. Chim. Acta 1996, 79, 1843. (c) Hollinshead, S. P. Tetrahedron Lett. 1996, 37, 9157. (d) Tokuda, M.; Fujita, H.; Nitta, M.; Suginome, H. Heterocycles 1996, 42, 385. (e) Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. (f) Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200. (g) Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. (i) Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895. (j) Alvarez-Ibarra, C.; Csaky, A. G.; Lopez de Silanes, I.; Quiroga, M. L. J. Org. Chem. 1997, 62, 479.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4200
    • Kercher, T.1    Livinghouse, T.2
  • 22
    • 0029915784 scopus 로고    scopus 로고
    • For recent examples, see: (a) Coldham, I.; Hufton, R. Tetrahe-dron 1996, 52, 12541. (b) Steiner, A.; Wessig, P.; Polborn, K. Helv. Chim. Acta 1996, 79, 1843. (c) Hollinshead, S. P. Tetrahedron Lett. 1996, 37, 9157. (d) Tokuda, M.; Fujita, H.; Nitta, M.; Suginome, H. Heterocycles 1996, 42, 385. (e) Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. (f) Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200. (g) Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. (i) Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895. (j) Alvarez-Ibarra, C.; Csaky, A. G.; Lopez de Silanes, I.; Quiroga, M. L. J. Org. Chem. 1997, 62, 479.
    • (1996) J. Org. Chem. , vol.61 , pp. 2268
    • Harvey, D.F.1    Sigano, D.M.2
  • 23
    • 0001338814 scopus 로고    scopus 로고
    • For recent examples, see: (a) Coldham, I.; Hufton, R. Tetrahe-dron 1996, 52, 12541. (b) Steiner, A.; Wessig, P.; Polborn, K. Helv. Chim. Acta 1996, 79, 1843. (c) Hollinshead, S. P. Tetrahedron Lett. 1996, 37, 9157. (d) Tokuda, M.; Fujita, H.; Nitta, M.; Suginome, H. Heterocycles 1996, 42, 385. (e) Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. (f) Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200. (g) Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. (i) Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895. (j) Alvarez-Ibarra, C.; Csaky, A. G.; Lopez de Silanes, I.; Quiroga, M. L. J. Org. Chem. 1997, 62, 479.
    • (1996) J. Org. Chem. , vol.61 , pp. 3584
    • Larock, R.C.1    Hightower, T.R.2    Hasvold, L.A.3    Peterson, K.P.4
  • 24
    • 0000960319 scopus 로고    scopus 로고
    • For recent examples, see: (a) Coldham, I.; Hufton, R. Tetrahe-dron 1996, 52, 12541. (b) Steiner, A.; Wessig, P.; Polborn, K. Helv. Chim. Acta 1996, 79, 1843. (c) Hollinshead, S. P. Tetrahedron Lett. 1996, 37, 9157. (d) Tokuda, M.; Fujita, H.; Nitta, M.; Suginome, H. Heterocycles 1996, 42, 385. (e) Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. (f) Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200. (g) Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. (i) Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895. (j) Alvarez-Ibarra, C.; Csaky, A. G.; Lopez de Silanes, I.; Quiroga, M. L. J. Org. Chem. 1997, 62, 479.
    • (1996) J. Org. Chem. , vol.61 , pp. 5895
    • Sole, D.1    Cancho, Y.2    Llebaria, A.3    Moreto, J.M.4    Delgado, A.5
  • 25
    • 0031025224 scopus 로고    scopus 로고
    • For recent examples, see: (a) Coldham, I.; Hufton, R. Tetrahe-dron 1996, 52, 12541. (b) Steiner, A.; Wessig, P.; Polborn, K. Helv. Chim. Acta 1996, 79, 1843. (c) Hollinshead, S. P. Tetrahedron Lett. 1996, 37, 9157. (d) Tokuda, M.; Fujita, H.; Nitta, M.; Suginome, H. Heterocycles 1996, 42, 385. (e) Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715. (f) Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200. (g) Harvey, D. F.; Sigano, D. M. J. Org. Chem. 1996, 61, 2268. (h) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584. (i) Sole, D.; Cancho, Y.; Llebaria, A.; Moreto, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895. (j) Alvarez-Ibarra, C.; Csaky, A. G.; Lopez de Silanes, I.; Quiroga, M. L. J. Org. Chem. 1997, 62, 479.
    • (1997) J. Org. Chem. , vol.62 , pp. 479
    • Alvarez-Ibarra, C.1    Csaky, A.G.2    Lopez De Silanes, I.3    Quiroga, M.L.4
  • 28
    • 0000293924 scopus 로고
    • For recent synthesis of N-tosylimines, see: (a) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366. (b) Love, B. E.; Raje, P. S.; Williams, T. C., II Synlett 1994, 493. (c) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1992, 57, 4777. (d) Trost, B. M.; Marrs, C. J. Org. Chem. 1991, 56, 6468. (e) Jennings, W. B.; Lovely, C. J. Tetrahedron 1991, 47, 5561.
    • (1995) J. Org. Chem. , vol.60 , pp. 7366
    • Georg, G.I.1    Harriman, G.C.B.2    Peterson, S.A.3
  • 29
    • 84988083468 scopus 로고
    • For recent synthesis of N-tosylimines, see: (a) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366. (b) Love, B. E.; Raje, P. S.; Williams, T. C., II Synlett 1994, 493. (c) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1992, 57, 4777. (d) Trost, B. M.; Marrs, C. J. Org. Chem. 1991, 56, 6468. (e) Jennings, W. B.; Lovely, C. J. Tetrahedron 1991, 47, 5561.
    • (1994) Synlett , pp. 493
    • Love, B.E.1    Raje, P.S.2    Williams II, T.C.3
  • 30
    • 0000350112 scopus 로고
    • For recent synthesis of N-tosylimines, see: (a) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366. (b) Love, B. E.; Raje, P. S.; Williams, T. C., II Synlett 1994, 493. (c) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1992, 57, 4777. (d) Trost, B. M.; Marrs, C. J. Org. Chem. 1991, 56, 6468. (e) Jennings, W. B.; Lovely, C. J. Tetrahedron 1991, 47, 5561.
    • (1992) J. Org. Chem. , vol.57 , pp. 4777
    • Boger, D.L.1    Corbett, W.L.2
  • 31
    • 0343758059 scopus 로고
    • For recent synthesis of N-tosylimines, see: (a) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366. (b) Love, B. E.; Raje, P. S.; Williams, T. C., II Synlett 1994, 493. (c) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1992, 57, 4777. (d) Trost, B. M.; Marrs, C. J. Org. Chem. 1991, 56, 6468. (e) Jennings, W. B.; Lovely, C. J. Tetrahedron 1991, 47, 5561.
    • (1991) J. Org. Chem. , vol.56 , pp. 6468
    • Trost, B.M.1    Marrs, C.2
  • 32
    • 0025912804 scopus 로고
    • For recent synthesis of N-tosylimines, see: (a) Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366. (b) Love, B. E.; Raje, P. S.; Williams, T. C., II Synlett 1994, 493. (c) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1992, 57, 4777. (d) Trost, B. M.; Marrs, C. J. Org. Chem. 1991, 56, 6468. (e) Jennings, W. B.; Lovely, C. J. Tetrahedron 1991, 47, 5561.
    • (1991) Tetrahedron , vol.47 , pp. 5561
    • Jennings, W.B.1    Lovely, C.J.2
  • 33
    • 0003719612 scopus 로고
    • Academic Press: San Diego
    • For reviews of six-membered rings, see: (a) Hetero Diels-Alder Methodology in organic synthesis; Boger, D. L., Weinreb, S. M., Eds.; Academic Press: San Diego, 1987. (b) Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 401.
    • (1987) Hetero Diels-Alder Methodology in Organic Synthesis
    • Boger, D.L.1    Weinreb, S.M.2
  • 34
    • 0000730407 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • For reviews of six-membered rings, see: (a) Hetero Diels-Alder Methodology in organic synthesis; Boger, D. L., Weinreb, S. M., Eds.; Academic Press: San Diego, 1987. (b) Weinreb, S. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 401.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 401
    • Weinreb, S.M.1
  • 35
    • 0343316156 scopus 로고
    • For the formation of five-membered rings, see: (a) Jiang, S.; Chen, T.; Turos, E. Organometallics 1995, 14, 4710. (b) Chen, T.; Jiang, S.; Turos, E. Tetrahedron Lett. 1994, 35, 8325. (c) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (d) Trost, B. M.; Matelich, M. C. J. Am. Chem. Soc. 1991, 113, 9007. (e) Saigo, K.; Shimada, S.; Hasegawa, M. Chem. Lett. 1990, 905.
    • (1995) Organometallics , vol.14 , pp. 4710
    • Jiang, S.1    Chen, T.2    Turos, E.3
  • 36
    • 0028151114 scopus 로고
    • For the formation of five-membered rings, see: (a) Jiang, S.; Chen, T.; Turos, E. Organometallics 1995, 14, 4710. (b) Chen, T.; Jiang, S.; Turos, E. Tetrahedron Lett. 1994, 35, 8325. (c) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (d) Trost, B. M.; Matelich, M. C. J. Am. Chem. Soc. 1991, 113, 9007. (e) Saigo, K.; Shimada, S.; Hasegawa, M. Chem. Lett. 1990, 905.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8325
    • Chen, T.1    Jiang, S.2    Turos, E.3
  • 37
    • 0010714873 scopus 로고
    • For the formation of five-membered rings, see: (a) Jiang, S.; Chen, T.; Turos, E. Organometallics 1995, 14, 4710. (b) Chen, T.; Jiang, S.; Turos, E. Tetrahedron Lett. 1994, 35, 8325. (c) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (d) Trost, B. M.; Matelich, M. C. J. Am. Chem. Soc. 1991, 113, 9007. (e) Saigo, K.; Shimada, S.; Hasegawa, M. Chem. Lett. 1990, 905.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 6636
    • Trost, B.M.1    Marrs, C.M.2
  • 38
    • 0000969630 scopus 로고
    • For the formation of five-membered rings, see: (a) Jiang, S.; Chen, T.; Turos, E. Organometallics 1995, 14, 4710. (b) Chen, T.; Jiang, S.; Turos, E. Tetrahedron Lett. 1994, 35, 8325. (c) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (d) Trost, B. M.; Matelich, M. C. J. Am. Chem. Soc. 1991, 113, 9007. (e) Saigo, K.; Shimada, S.; Hasegawa, M. Chem. Lett. 1990, 905.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9007
    • Trost, B.M.1    Matelich, M.C.2
  • 39
    • 0343316156 scopus 로고
    • For the formation of five-membered rings, see: (a) Jiang, S.; Chen, T.; Turos, E. Organometallics 1995, 14, 4710. (b) Chen, T.; Jiang, S.; Turos, E. Tetrahedron Lett. 1994, 35, 8325. (c) Trost, B. M.; Marrs, C. M. J. Am. Chem. Soc. 1993, 115, 6636. (d) Trost, B. M.; Matelich, M. C. J. Am. Chem. Soc. 1991, 113, 9007. (e) Saigo, K.; Shimada, S.; Hasegawa, M. Chem. Lett. 1990, 905.
    • (1990) Chem. Lett. , pp. 905
    • Saigo, K.1    Shimada, S.2    Hasegawa, M.3
  • 41
    • 0343752042 scopus 로고
    • Addition of carbon and oxygen nucleophiles to 2,3-butadienoates under the catalysis of a phosphine gave y-addition products regioselectively, see: Zhang, C.; Lu, X. Synlett 1995, 645. While this manuscript was under preparation, Trost et al. reported phosphine-catalyzed γ-addition of nitrogen pronucleophiles to methyl 2-butynoate, see: Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670.
    • (1995) Synlett , pp. 645
    • Zhang, C.1    Lu, X.2
  • 42
    • 0001334123 scopus 로고    scopus 로고
    • Addition of carbon and oxygen nucleophiles to 2,3-butadienoates under the catalysis of a phosphine gave y-addition products regioselectively, see: Zhang, C.; Lu, X. Synlett 1995, 645. While this manuscript was under preparation, Trost et al. reported phosphine-catalyzed γ-addition of nitrogen pronucleophiles to methyl 2-butynoate, see: Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670.
    • (1997) J. Org. Chem. , vol.62 , pp. 5670
    • Trost, B.M.1    Dake, G.R.2
  • 43
    • 0542429088 scopus 로고    scopus 로고
    • note
    • If a trapping reagent is less active than 1a, the self-cycloaddition product of 1a is formed. See ref 9.
  • 48
    • 0343752042 scopus 로고
    • The π orbitals of the two carbon-carbon double bonds in allenes are perpendicular to each other. In the initially generated intermediate 13, the orbital of the unshared electron pair is also perpendicular to the π orbital of the αβ,-carbon-carbon double bond. After a 90° rotation around the Cα-Cβ bond, the delocalized structure 13′ was formed, which results in the formation of 5. For a similar result, see: Zhang, C.; Lu, X. Synlett 1995, 645.
    • (1995) Synlett , pp. 645
    • Zhang, C.1    Lu, X.2
  • 65
    • 0542405185 scopus 로고    scopus 로고
    • note
    • 36 (Equation Presented)
  • 78
    • 84956100568 scopus 로고
    • Koenig, H.; Franke, A.; Frickel, F. F.; Steglich, W.; Engel, N. Ger. Offen. 2835439, 1980; Chem. Abstr. 1980, 93, 132363a.
    • (1980) Chem. Abstr. , vol.93


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