A Silicon Tether Approach for Addition of Functionalized Radicals to Chiral α-Hydroxyhydrazones: Diastereoselective Additions of Hydroxymethyl and Vinyl Synthons

Journal of Organic Chemistry

Volumn 69, Issue 3, 2004, Pages 863-875

  Friestad, Gregory K ^a   Massari, Sara E ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; HYDROXYLATION; POTASSIUM COMPOUNDS;

VINYL GROUPS;

SILICON;

2 HYDRAZINO 1,3 DIOL; ALPHA HYDROXYHYDRAZONE DERIVATIVE; BROMINE DERIVATIVE; BROMOMETHYL GROUP; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; HYDROXYL GROUP; HYDROXYMETHYL DERIVATIVE; POTASSIUM FLUORIDE; RADICAL; SILICON; TIN; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; ELIMINATION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0842307432     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035405r     Document Type: Article

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47. (f) Nitrone cycloadditions: Aggarwal, V. K.; Roseblade, S.; Alexander, R. Org. Biomol. Chem. 2003, 1, 684-691. Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444. Iwasa, S.; Maeda, H.; Nishiyama, K.; Tsushima, S.; Tsukamoto, Y.; Nishiyama, H. Tetrahedron 2002, 58, 8281-8287. Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Org. Lett. 2002, 4, 2457-2460. Denmark, S. E.; Gomez, L. Org. Lett. 2001, 3, 2907-2910.
48. (f) Nitrone cycloadditions: Aggarwal, V. K.; Roseblade, S.; Alexander, R. Org. Biomol. Chem. 2003, 1, 684-691. Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444. Iwasa, S.; Maeda, H.; Nishiyama, K.; Tsushima, S.; Tsukamoto, Y.; Nishiyama, H. Tetrahedron 2002, 58, 8281-8287. Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Org. Lett. 2002, 4, 2457-2460. Denmark, S. E.; Gomez, L. Org. Lett. 2001, 3, 2907-2910.
49. (f) Nitrone cycloadditions: Aggarwal, V. K.; Roseblade, S.; Alexander, R. Org. Biomol. Chem. 2003, 1, 684-691. Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444. Iwasa, S.; Maeda, H.; Nishiyama, K.; Tsushima, S.; Tsukamoto, Y.; Nishiyama, H. Tetrahedron 2002, 58, 8281-8287. Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Org. Lett. 2002, 4, 2457-2460. Denmark, S. E.; Gomez, L. Org. Lett. 2001, 3, 2907-2910.
50. (f) Nitrone cycloadditions: Aggarwal, V. K.; Roseblade, S.; Alexander, R. Org. Biomol. Chem. 2003, 1, 684-691. Hanessian, S.; Bayrakdarian, M. Tetrahedron Lett. 2002, 43, 9441-9444. Iwasa, S.; Maeda, H.; Nishiyama, K.; Tsushima, S.; Tsukamoto, Y.; Nishiyama, H. Tetrahedron 2002, 58, 8281-8287. Mita, T.; Ohtsuki, N.; Ikeno, T.; Yamada, T. Org. Lett. 2002, 4, 2457-2460. Denmark, S. E.; Gomez, L. Org. Lett. 2001, 3, 2907-2910.
51. (g) Organozinc additions: Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692-1693. Hermanns, N.; Dahmen, S.; Bolm, C.; Brase S. Angew. Chem., Int. Ed. 2002, 41, 3692-3694. Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409-10410.
52. (g) Organozinc additions: Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692-1693. Hermanns, N.; Dahmen, S.; Bolm, C.; Brase S. Angew. Chem., Int. Ed. 2002, 41, 3692-3694. Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409-10410.
53. (g) Organozinc additions: Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692-1693. Hermanns, N.; Dahmen, S.; Bolm, C.; Brase S. Angew. Chem., Int. Ed. 2002, 41, 3692-3694. Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409-10410.
54. (h) Allylsilane additions: Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 6610-6611. Friestad, G. K.; Ding, H. Angew. Chem., Int. Ed. 2001, 40, 4491-4493.
55. (h) Allylsilane additions: Kobayashi, S.; Ogawa, C.; Konishi, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 6610-6611. Friestad, G. K.; Ding, H. Angew. Chem., Int. Ed. 2001, 40, 4491-4493.
56. (i) Alkynylmetal additions: Fassler, R.; Frantz, D. E.; Oetiker, J.; Carreira, E. M. Angew. Chem., Int. Ed. 2002, 41, 3054-3056. Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535-2538. Wei, C. M. ; Li, C. J. J. Am. Chem. Soc. 2002, 124, 5638-5639.
57. (i) Alkynylmetal additions: Fassler, R.; Frantz, D. E.; Oetiker, J.; Carreira, E. M. Angew. Chem., Int. Ed. 2002, 41, 3054-3056. Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535-2538. Wei, C. M. ; Li, C. J. J. Am. Chem. Soc. 2002, 124, 5638-5639.
58. (i) Alkynylmetal additions: Fassler, R.; Frantz, D. E.; Oetiker, J.; Carreira, E. M. Angew. Chem., Int. Ed. 2002, 41, 3054-3056. Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 2535-2538. Wei, C. M. ; Li, C. J. J. Am. Chem. Soc. 2002, 124, 5638-5639.
59. (j) Friedel-Crafts-type addition: Ge, C.-S.; Wang, D. Synlett 2002, 37-42. Saaby, S.; Bayon, P.; Aburel, P. S.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 4352-4361.
60. (j) Friedel-Crafts-type addition: Ge, C.-S.; Wang, D. Synlett 2002, 37-42. Saaby, S.; Bayon, P.; Aburel, P. S.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 4352-4361.
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62. (b) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: New York; 1995.
63. (c) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163-171.
64. (d) Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2563-2579.
65. (e) Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856.
66. (f) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237-1286.
67. (g) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986.
68. (h) Hart, D. J. Science 1984, 223, 883-887.
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70. (b) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543-17594.
71. (c) For recent examples of intermolecular addition to C=N bonds, see refs 12-14. See also: Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797-1799. Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772-1775. Halland, N. Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 1290-1295. Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987. Recent examples of cyclizations of C=N bonds: Ryu, I.; Miyazato, H.; Kuriyama, H.; Matsu, K.; Tojino, M.; Fukuyama, T.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2003, 125, 5632-5633. Alajarin, M.; Vidal, A.; Ortin, M.-M. Tetrahedron Lett. 2003, 44, 3027-3030. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163-168. Miyabe, H.; Nishiki, A.; Naito, T. Chem. Pharm. Bull. 2003, 51, 100-103. Falzon C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338-2339. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Prabharakaran, E. N.; Nugent, B. M.; Williams, A. L.; Nailor, K. E.; Johnston, J. N. Org. Lett. 2002, 4, 4197-4200. Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouétard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem. 2001, 66, 1233-1241. Nicolaou, K. C.; Huang, X.; Giuseppone, N.; Rao, P. B.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705-4709. Johnston, J. N.; Plotkin, M. A.; Viswanathan, R. ; Prabharakaran, E. N. Org. Lett. 2001, 3, 1009-1011.
72. (c) For recent examples of intermolecular addition to C=N bonds, see refs 12-14. See also: Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797-1799. Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772-1775. Halland, N. Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 1290-1295. Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987. Recent examples of cyclizations of C=N bonds: Ryu, I.; Miyazato, H.; Kuriyama, H.; Matsu, K.; Tojino, M.; Fukuyama, T.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2003, 125, 5632-5633. Alajarin, M.; Vidal, A.; Ortin, M.-M. Tetrahedron Lett. 2003, 44, 3027-3030. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163-168. Miyabe, H.; Nishiki, A.; Naito, T. Chem. Pharm. Bull. 2003, 51, 100-103. Falzon C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338-2339. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Prabharakaran, E. N.; Nugent, B. M.; Williams, A. L.; Nailor, K. E.; Johnston, J. N. Org. Lett. 2002, 4, 4197-4200. Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouétard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem. 2001, 66, 1233-1241. Nicolaou, K. C.; Huang, X.; Giuseppone, N.; Rao, P. B.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705-4709. Johnston, J. N.; Plotkin, M. A.; Viswanathan, R. ; Prabharakaran, E. N. Org. Lett. 2001, 3, 1009-1011.
73. (c) For recent examples of intermolecular addition to C=N bonds, see refs 12-14. See also: Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797-1799. Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772-1775. Halland, N. Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 1290-1295. Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987. Recent examples of cyclizations of C=N bonds: Ryu, I.; Miyazato, H.; Kuriyama, H.; Matsu, K.; Tojino, M.; Fukuyama, T.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2003, 125, 5632-5633. Alajarin, M.; Vidal, A.; Ortin, M.-M. Tetrahedron Lett. 2003, 44, 3027-3030. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163-168. Miyabe, H.; Nishiki, A.; Naito, T. Chem. Pharm. Bull. 2003, 51, 100-103. Falzon C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338-2339. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Prabharakaran, E. N.; Nugent, B. M.; Williams, A. L.; Nailor, K. E.; Johnston, J. N. Org. Lett. 2002, 4, 4197-4200. Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouétard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem. 2001, 66, 1233-1241. Nicolaou, K. C.; Huang, X.; Giuseppone, N.; Rao, P. B.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705-4709. Johnston, J. N.; Plotkin, M. A.; Viswanathan, R. ; Prabharakaran, E. N. Org. Lett. 2001, 3, 1009-1011.
74. (c) For recent examples of intermolecular addition to C=N bonds, see refs 12-14. See also: Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797-1799. Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772-1775. Halland, N. Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 1290-1295. Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987. Recent examples of cyclizations of C=N bonds: Ryu, I.; Miyazato, H.; Kuriyama, H.; Matsu, K.; Tojino, M.; Fukuyama, T.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2003, 125, 5632-5633. Alajarin, M.; Vidal, A.; Ortin, M.-M. Tetrahedron Lett. 2003, 44, 3027-3030. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163-168. Miyabe, H.; Nishiki, A.; Naito, T. Chem. Pharm. Bull. 2003, 51, 100-103. Falzon C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338-2339. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Prabharakaran, E. N.; Nugent, B. M.; Williams, A. L.; Nailor, K. E.; Johnston, J. N. Org. Lett. 2002, 4, 4197-4200. Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouétard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem. 2001, 66, 1233-1241. Nicolaou, K. C.; Huang, X.; Giuseppone, N.; Rao, P. B.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705-4709. Johnston, J. N.; Plotkin, M. A.; Viswanathan, R. ; Prabharakaran, E. N. Org. Lett. 2001, 3, 1009-1011.
75. (c) For recent examples of intermolecular addition to C=N bonds, see refs 12-14. See also: Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797-1799. Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772-1775. Halland, N. Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 1290-1295. Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987. Recent examples of cyclizations of C=N bonds: Ryu, I.; Miyazato, H.; Kuriyama, H.; Matsu, K.; Tojino, M.; Fukuyama, T.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2003, 125, 5632-5633. Alajarin, M.; Vidal, A.; Ortin, M.-M. Tetrahedron Lett. 2003, 44, 3027-3030. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163-168. Miyabe, H.; Nishiki, A.; Naito, T. Chem. Pharm. Bull. 2003, 51, 100-103. Falzon C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338-2339. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Prabharakaran, E. N.; Nugent, B. M.; Williams, A. L.; Nailor, K. E.; Johnston, J. N. Org. Lett. 2002, 4, 4197-4200. Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouétard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem. 2001, 66, 1233-1241. Nicolaou, K. C.; Huang, X.; Giuseppone, N.; Rao, P. B.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705-4709. Johnston, J. N.; Plotkin, M. A.; Viswanathan, R. ; Prabharakaran, E. N. Org. Lett. 2001, 3, 1009-1011.
76. (c) For recent examples of intermolecular addition to C=N bonds, see refs 12-14. See also: Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797-1799. Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772-1775. Halland, N. Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 1290-1295. Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987. Recent examples of cyclizations of C=N bonds: Ryu, I.; Miyazato, H.; Kuriyama, H.; Matsu, K.; Tojino, M.; Fukuyama, T.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2003, 125, 5632-5633. Alajarin, M.; Vidal, A.; Ortin, M.-M. Tetrahedron Lett. 2003, 44, 3027-3030. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163-168. Miyabe, H.; Nishiki, A.; Naito, T. Chem. Pharm. Bull. 2003, 51, 100-103. Falzon C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338-2339. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Prabharakaran, E. N.; Nugent, B. M.; Williams, A. L.; Nailor, K. E.; Johnston, J. N. Org. Lett. 2002, 4, 4197-4200. Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouétard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem. 2001, 66, 1233-1241. Nicolaou, K. C.; Huang, X.; Giuseppone, N.; Rao, P. B.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705-4709. Johnston, J. N.; Plotkin, M. A.; Viswanathan, R. ; Prabharakaran, E. N. Org. Lett. 2001, 3, 1009-1011.
77. (c) For recent examples of intermolecular addition to C=N bonds, see refs 12-14. See also: Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797-1799. Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772-1775. Halland, N. Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 1290-1295. Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987. Recent examples of cyclizations of C=N bonds: Ryu, I.; Miyazato, H.; Kuriyama, H.; Matsu, K.; Tojino, M.; Fukuyama, T.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2003, 125, 5632-5633. Alajarin, M.; Vidal, A.; Ortin, M.-M. Tetrahedron Lett. 2003, 44, 3027-3030. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163-168. Miyabe, H.; Nishiki, A.; Naito, T. Chem. Pharm. Bull. 2003, 51, 100-103. Falzon C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338-2339. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Prabharakaran, E. N.; Nugent, B. M.; Williams, A. L.; Nailor, K. E.; Johnston, J. N. Org. Lett. 2002, 4, 4197-4200. Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouétard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem. 2001, 66, 1233-1241. Nicolaou, K. C.; Huang, X.; Giuseppone, N.; Rao, P. B.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705-4709. Johnston, J. N.; Plotkin, M. A.; Viswanathan, R. ; Prabharakaran, E. N. Org. Lett. 2001, 3, 1009-1011.
78. (c) For recent examples of intermolecular addition to C=N bonds, see refs 12-14. See also: Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797-1799. Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772-1775. Halland, N. Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 1290-1295. Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987. Recent examples of cyclizations of C=N bonds: Ryu, I.; Miyazato, H.; Kuriyama, H.; Matsu, K.; Tojino, M.; Fukuyama, T.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2003, 125, 5632-5633. Alajarin, M.; Vidal, A.; Ortin, M.-M. Tetrahedron Lett. 2003, 44, 3027-3030. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163-168. Miyabe, H.; Nishiki, A.; Naito, T. Chem. Pharm. Bull. 2003, 51, 100-103. Falzon C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338-2339. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Prabharakaran, E. N.; Nugent, B. M.; Williams, A. L.; Nailor, K. E.; Johnston, J. N. Org. Lett. 2002, 4, 4197-4200. Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouétard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem. 2001, 66, 1233-1241. Nicolaou, K. C.; Huang, X.; Giuseppone, N.; Rao, P. B.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705-4709. Johnston, J. N.; Plotkin, M. A.; Viswanathan, R. ; Prabharakaran, E. N. Org. Lett. 2001, 3, 1009-1011.
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81. (c) For recent examples of intermolecular addition to C=N bonds, see refs 12-14. See also: Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797-1799. Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772-1775. Halland, N. Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 1290-1295. Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987. Recent examples of cyclizations of C=N bonds: Ryu, I.; Miyazato, H.; Kuriyama, H.; Matsu, K.; Tojino, M.; Fukuyama, T.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2003, 125, 5632-5633. Alajarin, M.; Vidal, A.; Ortin, M.-M. Tetrahedron Lett. 2003, 44, 3027-3030. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163-168. Miyabe, H.; Nishiki, A.; Naito, T. Chem. Pharm. Bull. 2003, 51, 100-103. Falzon C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338-2339. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Prabharakaran, E. N.; Nugent, B. M.; Williams, A. L.; Nailor, K. E.; Johnston, J. N. Org. Lett. 2002, 4, 4197-4200. Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouétard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem. 2001, 66, 1233-1241. Nicolaou, K. C.; Huang, X.; Giuseppone, N.; Rao, P. B.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705-4709. Johnston, J. N.; Plotkin, M. A.; Viswanathan, R. ; Prabharakaran, E. N. Org. Lett. 2001, 3, 1009-1011.
82. (c) For recent examples of intermolecular addition to C=N bonds, see refs 12-14. See also: Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797-1799. Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509-3511. Masson, G.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2002, 41, 1772-1775. Halland, N. Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 2001, 1290-1295. Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987. Recent examples of cyclizations of C=N bonds: Ryu, I.; Miyazato, H.; Kuriyama, H.; Matsu, K.; Tojino, M.; Fukuyama, T.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2003, 125, 5632-5633. Alajarin, M.; Vidal, A.; Ortin, M.-M. Tetrahedron Lett. 2003, 44, 3027-3030. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163-168. Miyabe, H.; Nishiki, A.; Naito, T. Chem. Pharm. Bull. 2003, 51, 100-103. Falzon C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338-2339. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Prabharakaran, E. N.; Nugent, B. M.; Williams, A. L.; Nailor, K. E.; Johnston, J. N. Org. Lett. 2002, 4, 4197-4200. Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouétard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem. 2001, 66, 1233-1241. Nicolaou, K. C.; Huang, X.; Giuseppone, N.; Rao, P. B.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705-4709. Johnston, J. N.; Plotkin, M. A.; Viswanathan, R. ; Prabharakaran, E. N. Org. Lett. 2001, 3, 1009-1011.
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100. Reviews: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338. Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
101. Reviews: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338. Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
102. Reviews: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338. Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
103. Reviews: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338. Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
104. For some recent examples, see: (a) silylformylation: Zacuto, M. J.; O'Malley, S. J.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7890-7891.
105. (b) Hydrosilylation: Paquette, L. A.; Yang, J.; Long, Y. O. J. Am. Chem. Soc. 2002, 124, 6542-6543.
106. (c) Diene metathesis: Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734-1737. Denmark, S. E.; Yang, S.-M. J. Am. Chem. Soc. 2002, 124, 2102-2103. Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099.
107. (c) Diene metathesis: Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734-1737. Denmark, S. E.; Yang, S.-M. J. Am. Chem. Soc. 2002, 124, 2102-2103. Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099.
108. (c) Diene metathesis: Evans, P. A.; Cui, J.; Buffone, G. P. Angew. Chem., Int. Ed. 2003, 42, 1734-1737. Denmark, S. E.; Yang, S.-M. J. Am. Chem. Soc. 2002, 124, 2102-2103. Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099.
109. (d) Enyne metathesis: Semeril, D.; Cleran, M.; Perez, A. J.; Bruneau, C. ; Dixneuf, P. H. J. Mol. Catal. A 2002, 190, 9-25.
110. Yao, Q. Org. Lett. 2001, 3, 2069-2072.
111. (e) Pd-catalyzed cross-coupling: Quan, L. G.; Cha, J. K. J. Am. Chem. Soc. 2002, 124, 12424-12425.
112. (f) Cyclocarbonylation: Pearson, A. J.; Kim, J. B. Org. Lett. 2002, 4, 2837-2840. Brummond, K. M.; Sill, P. C.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43, 3735-3738. Reichwein, J. F.; Iacono, S. T.; Patel, M. C.; Pagenkopf, B. L. Tetrahedron Lett. 2002, 43, 3739-3741.
113. (f) Cyclocarbonylation: Pearson, A. J.; Kim, J. B. Org. Lett. 2002, 4, 2837-2840. Brummond, K. M.; Sill, P. C.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43, 3735-3738. Reichwein, J. F.; Iacono, S. T.; Patel, M. C.; Pagenkopf, B. L. Tetrahedron Lett. 2002, 43, 3739-3741.
114. (f) Cyclocarbonylation: Pearson, A. J.; Kim, J. B. Org. Lett. 2002, 4, 2837-2840. Brummond, K. M.; Sill, P. C.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43, 3735-3738. Reichwein, J. F.; Iacono, S. T.; Patel, M. C.; Pagenkopf, B. L. Tetrahedron Lett. 2002, 43, 3739-3741.
115. (g) Ni-catalyzed cyclization: Lozanov, M.; Montgomery, J. Tetrahedron Lett. 2001, 42, 3259-3261.
116. (h) [3 + 2] nitrone cycloaddition: Ishikawa, T.; Kudo, T.; Shigemori, K. ; Saito, S. J. Am. Chem. Soc. 2000, 122, 7633-7637. Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046-3056.
117. (h) [3 + 2] nitrone cycloaddition: Ishikawa, T.; Kudo, T.; Shigemori, K. ; Saito, S. J. Am. Chem. Soc. 2000, 122, 7633-7637. Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046-3056.
118. (i) O-Formylation: Cohen, Y.; Kotlyar, V.; Koeller, S.; Lellouche, J.-P. Synlett 2001, 1543-1546.
119. (j) Oxocarbenium allylation: Pilli, R.; Riatto, V. B. Tetrahedron: Asymmetry 2000, 11, 3675-3686.
120. (k) Many examples of earlier work appear in several excellent reviews cited in ref 15b.
121. A variety of α-hydroxy esters are available in one or two steps from commercially available α-hydroxy acids or α-amino acids.
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132. Oh, J. S.; Park, D. Y.; Song, B. S.; Bae, J. G.; Yoon, S. W.; Kim, Y. G. Tetrahedron Lett. 2002, 43, 7209-7212. Ncube, A.; Park, S. B.; Chong, J. M. J. Org. Chem. 2002, 67, 3625-3636. Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510-12517. Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. Deng, J. G.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627-638. Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271-3274. Falb, E.; Nudelman, A.; Hassner, A. Synth. Commun. 1993, 23, 2839-2844. Moreno-Mañas, M.; Padros, I. J. Heterocycl. Chem. 1993, 30, 1235-1239. Foglia, T. A.; Swern, D. J. Org. Chem. 1968, 34, 1680-1684.
133. Oh, J. S.; Park, D. Y.; Song, B. S.; Bae, J. G.; Yoon, S. W.; Kim, Y. G. Tetrahedron Lett. 2002, 43, 7209-7212. Ncube, A.; Park, S. B.; Chong, J. M. J. Org. Chem. 2002, 67, 3625-3636. Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510-12517. Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. Deng, J. G.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627-638. Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271-3274. Falb, E.; Nudelman, A.; Hassner, A. Synth. Commun. 1993, 23, 2839-2844. Moreno-Mañas, M.; Padros, I. J. Heterocycl. Chem. 1993, 30, 1235-1239. Foglia, T. A.; Swern, D. J. Org. Chem. 1968, 34, 1680-1684.
134. Oh, J. S.; Park, D. Y.; Song, B. S.; Bae, J. G.; Yoon, S. W.; Kim, Y. G. Tetrahedron Lett. 2002, 43, 7209-7212. Ncube, A.; Park, S. B.; Chong, J. M. J. Org. Chem. 2002, 67, 3625-3636. Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510-12517. Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. Deng, J. G.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627-638. Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271-3274. Falb, E.; Nudelman, A.; Hassner, A. Synth. Commun. 1993, 23, 2839-2844. Moreno-Mañas, M.; Padros, I. J. Heterocycl. Chem. 1993, 30, 1235-1239. Foglia, T. A.; Swern, D. J. Org. Chem. 1968, 34, 1680-1684.
135. Oh, J. S.; Park, D. Y.; Song, B. S.; Bae, J. G.; Yoon, S. W.; Kim, Y. G. Tetrahedron Lett. 2002, 43, 7209-7212. Ncube, A.; Park, S. B.; Chong, J. M. J. Org. Chem. 2002, 67, 3625-3636. Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510-12517. Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. Deng, J. G.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627-638. Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271-3274. Falb, E.; Nudelman, A.; Hassner, A. Synth. Commun. 1993, 23, 2839-2844. Moreno-Mañas, M.; Padros, I. J. Heterocycl. Chem. 1993, 30, 1235-1239. Foglia, T. A.; Swern, D. J. Org. Chem. 1968, 34, 1680-1684.
136. Oh, J. S.; Park, D. Y.; Song, B. S.; Bae, J. G.; Yoon, S. W.; Kim, Y. G. Tetrahedron Lett. 2002, 43, 7209-7212. Ncube, A.; Park, S. B.; Chong, J. M. J. Org. Chem. 2002, 67, 3625-3636. Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510-12517. Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. Deng, J. G.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627-638. Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271-3274. Falb, E.; Nudelman, A.; Hassner, A. Synth. Commun. 1993, 23, 2839-2844. Moreno-Mañas, M.; Padros, I. J. Heterocycl. Chem. 1993, 30, 1235-1239. Foglia, T. A.; Swern, D. J. Org. Chem. 1968, 34, 1680-1684.
137. Oh, J. S.; Park, D. Y.; Song, B. S.; Bae, J. G.; Yoon, S. W.; Kim, Y. G. Tetrahedron Lett. 2002, 43, 7209-7212. Ncube, A.; Park, S. B.; Chong, J. M. J. Org. Chem. 2002, 67, 3625-3636. Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510-12517. Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. Deng, J. G.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627-638. Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271-3274. Falb, E.; Nudelman, A.; Hassner, A. Synth. Commun. 1993, 23, 2839-2844. Moreno-Mañas, M.; Padros, I. J. Heterocycl. Chem. 1993, 30, 1235-1239. Foglia, T. A.; Swern, D. J. Org. Chem. 1968, 34, 1680-1684.
138. Oh, J. S.; Park, D. Y.; Song, B. S.; Bae, J. G.; Yoon, S. W.; Kim, Y. G. Tetrahedron Lett. 2002, 43, 7209-7212. Ncube, A.; Park, S. B.; Chong, J. M. J. Org. Chem. 2002, 67, 3625-3636. Sugiura, M.; Hagio, H.; Hirabayashi, R.; Kobayashi, S. J. Am. Chem. Soc. 2001, 123, 12510-12517. Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322. Deng, J. G.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627-638. Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271-3274. Falb, E.; Nudelman, A.; Hassner, A. Synth. Commun. 1993, 23, 2839-2844. Moreno-Mañas, M.; Padros, I. J. Heterocycl. Chem. 1993, 30, 1235-1239. Foglia, T. A.; Swern, D. J. Org. Chem. 1968, 34, 1680-1684.
139. Aldehyde hydrazones are generally obtained as E isomers. Enders, D. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984, pp 275-339.
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141. Fleming, I. Chemtracts-Org. Chem. 1996, 9, 1-64.
142. Coupling constants of acetonides have previously been used to elucidate the relative configurations of various 2-amino-1,3-diols. Devijver, C.; Salmoun, M.; Daloze, D.; Braekman, J. C.; De Weerdt, W. H.; De Kluijver, M. J.; Gomez, R. J. Nat. Prod. 2000, 63, 978-980. Mancini, I.; Guella, G.; Debitus, C.; Pietra, F. Helv. Chim. Acta 1994, 77, 51-58. Mori, K.; Uenishi, K. Liebigs Ann. Chem. 1994, 41-48. Barrett, A. G. M.; Rys, D. J. Chem. Soc. Perkin Trans. 1 1995, 1009-1017. Han, B. H.; Kim, J. C.; Park, M. K.; Park, J. H.; Go, H. J.; Yang, H. D.; Suh, D.-Y.; Kang, Y.-H. Heterocycles 1995, 41, 1909-1914. Herold, P.; Helv. Chim. Acta 1988, 71, 354-362.
143. Coupling constants of acetonides have previously been used to elucidate the relative configurations of various 2-amino-1,3-diols. Devijver, C.; Salmoun, M.; Daloze, D.; Braekman, J. C.; De Weerdt, W. H.; De Kluijver, M. J.; Gomez, R. J. Nat. Prod. 2000, 63, 978-980. Mancini, I.; Guella, G.; Debitus, C.; Pietra, F. Helv. Chim. Acta 1994, 77, 51-58. Mori, K.; Uenishi, K. Liebigs Ann. Chem. 1994, 41-48. Barrett, A. G. M.; Rys, D. J. Chem. Soc. Perkin Trans. 1 1995, 1009-1017. Han, B. H.; Kim, J. C.; Park, M. K.; Park, J. H.; Go, H. J.; Yang, H. D.; Suh, D.-Y.; Kang, Y.-H. Heterocycles 1995, 41, 1909-1914. Herold, P.; Helv. Chim. Acta 1988, 71, 354-362.
144. Coupling constants of acetonides have previously been used to elucidate the relative configurations of various 2-amino-1,3-diols. Devijver, C.; Salmoun, M.; Daloze, D.; Braekman, J. C.; De Weerdt, W. H.; De Kluijver, M. J.; Gomez, R. J. Nat. Prod. 2000, 63, 978-980. Mancini, I.; Guella, G.; Debitus, C.; Pietra, F. Helv. Chim. Acta 1994, 77, 51-58. Mori, K.; Uenishi, K. Liebigs Ann. Chem. 1994, 41-48. Barrett, A. G. M.; Rys, D. J. Chem. Soc. Perkin Trans. 1 1995, 1009-1017. Han, B. H.; Kim, J. C.; Park, M. K.; Park, J. H.; Go, H. J.; Yang, H. D.; Suh, D.-Y.; Kang, Y.-H. Heterocycles 1995, 41, 1909-1914. Herold, P.; Helv. Chim. Acta 1988, 71, 354-362.
145. Coupling constants of acetonides have previously been used to elucidate the relative configurations of various 2-amino-1,3-diols. Devijver, C.; Salmoun, M.; Daloze, D.; Braekman, J. C.; De Weerdt, W. H.; De Kluijver, M. J.; Gomez, R. J. Nat. Prod. 2000, 63, 978-980. Mancini, I.; Guella, G.; Debitus, C.; Pietra, F. Helv. Chim. Acta 1994, 77, 51-58. Mori, K.; Uenishi, K. Liebigs Ann. Chem. 1994, 41-48. Barrett, A. G. M.; Rys, D. J. Chem. Soc. Perkin Trans. 1 1995, 1009-1017. Han, B. H.; Kim, J. C.; Park, M. K.; Park, J. H.; Go, H. J.; Yang, H. D.; Suh, D.-Y.; Kang, Y.-H. Heterocycles 1995, 41, 1909-1914. Herold, P.; Helv. Chim. Acta 1988, 71, 354-362.
146. Coupling constants of acetonides have previously been used to elucidate the relative configurations of various 2-amino-1,3-diols. Devijver, C.; Salmoun, M.; Daloze, D.; Braekman, J. C.; De Weerdt, W. H.; De Kluijver, M. J.; Gomez, R. J. Nat. Prod. 2000, 63, 978-980. Mancini, I.; Guella, G.; Debitus, C.; Pietra, F. Helv. Chim. Acta 1994, 77, 51-58. Mori, K.; Uenishi, K. Liebigs Ann. Chem. 1994, 41-48. Barrett, A. G. M.; Rys, D. J. Chem. Soc. Perkin Trans. 1 1995, 1009-1017. Han, B. H.; Kim, J. C.; Park, M. K.; Park, J. H.; Go, H. J.; Yang, H. D.; Suh, D.-Y.; Kang, Y.-H. Heterocycles 1995, 41, 1909-1914. Herold, P.; Helv. Chim. Acta 1988, 71, 354-362.
147. Coupling constants of acetonides have previously been used to elucidate the relative configurations of various 2-amino-1,3-diols. Devijver, C.; Salmoun, M.; Daloze, D.; Braekman, J. C.; De Weerdt, W. H.; De Kluijver, M. J.; Gomez, R. J. Nat. Prod. 2000, 63, 978-980. Mancini, I.; Guella, G.; Debitus, C.; Pietra, F. Helv. Chim. Acta 1994, 77, 51-58. Mori, K.; Uenishi, K. Liebigs Ann. Chem. 1994, 41-48. Barrett, A. G. M.; Rys, D. J. Chem. Soc. Perkin Trans. 1 1995, 1009-1017. Han, B. H.; Kim, J. C.; Park, M. K.; Park, J. H.; Go, H. J.; Yang, H. D.; Suh, D.-Y.; Kang, Y.-H. Heterocycles 1995, 41, 1909-1914. Herold, P.; Helv. Chim. Acta 1988, 71, 354-362.
148. Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9-17.
149. Reviews: Miyata, O.; Naito, T. C. R. Acad. Sci. Paris, Chim. 2001, 4, 401-421. Naito, T. Heterocycles 1999, 50, 505-541. For selected recent examples, see: Miyata, O.; Nakajima, E.; Naito, T. Chem. Pharm. Bull. 2001, 49, 213-224. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199-6207. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275-280. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515-1518. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547-4550. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749-6750.
150. Reviews: Miyata, O.; Naito, T. C. R. Acad. Sci. Paris, Chim. 2001, 4, 401-421. Naito, T. Heterocycles 1999, 50, 505-541. For selected recent examples, see: Miyata, O.; Nakajima, E.; Naito, T. Chem. Pharm. Bull. 2001, 49, 213-224. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199-6207. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275-280. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515-1518. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547-4550. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749-6750.
151. Reviews: Miyata, O.; Naito, T. C. R. Acad. Sci. Paris, Chim. 2001, 4, 401-421. Naito, T. Heterocycles 1999, 50, 505-541. For selected recent examples, see: Miyata, O.; Nakajima, E.; Naito, T. Chem. Pharm. Bull. 2001, 49, 213-224. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199-6207. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275-280. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515-1518. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547-4550. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749-6750.
152. Reviews: Miyata, O.; Naito, T. C. R. Acad. Sci. Paris, Chim. 2001, 4, 401-421. Naito, T. Heterocycles 1999, 50, 505-541. For selected recent examples, see: Miyata, O.; Nakajima, E.; Naito, T. Chem. Pharm. Bull. 2001, 49, 213-224. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199-6207. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275-280. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515-1518. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547-4550. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749-6750.
153. Reviews: Miyata, O.; Naito, T. C. R. Acad. Sci. Paris, Chim. 2001, 4, 401-421. Naito, T. Heterocycles 1999, 50, 505-541. For selected recent examples, see: Miyata, O.; Nakajima, E.; Naito, T. Chem. Pharm. Bull. 2001, 49, 213-224. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199-6207. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275-280. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515-1518. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547-4550. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749-6750.
154. Reviews: Miyata, O.; Naito, T. C. R. Acad. Sci. Paris, Chim. 2001, 4, 401-421. Naito, T. Heterocycles 1999, 50, 505-541. For selected recent examples, see: Miyata, O.; Nakajima, E.; Naito, T. Chem. Pharm. Bull. 2001, 49, 213-224. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199-6207. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275-280. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515-1518. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547-4550. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749-6750.
155. Reviews: Miyata, O.; Naito, T. C. R. Acad. Sci. Paris, Chim. 2001, 4, 401-421. Naito, T. Heterocycles 1999, 50, 505-541. For selected recent examples, see: Miyata, O.; Nakajima, E.; Naito, T. Chem. Pharm. Bull. 2001, 49, 213-224. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199-6207. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275-280. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515-1518. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547-4550. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749-6750.
156. Reviews: Miyata, O.; Naito, T. C. R. Acad. Sci. Paris, Chim. 2001, 4, 401-421. Naito, T. Heterocycles 1999, 50, 505-541. For selected recent examples, see: Miyata, O.; Nakajima, E.; Naito, T. Chem. Pharm. Bull. 2001, 49, 213-224. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199-6207. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275-280. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515-1518. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547-4550. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749-6750.
157. Reviews: Miyata, O.; Naito, T. C. R. Acad. Sci. Paris, Chim. 2001, 4, 401-421. Naito, T. Heterocycles 1999, 50, 505-541. For selected recent examples, see: Miyata, O.; Nakajima, E.; Naito, T. Chem. Pharm. Bull. 2001, 49, 213-224. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479. Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199-6207. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275-280. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515-1518. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547-4550. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749-6750.
158. For cyclizations of C=N acceptors initiated by intermolecular addition of alkyl radicals, see: Miyabe, H.; Fujii, K.; Goto, T.; Naito, T. Org. Lett. 2000, 2, 4071-4074. Miyabe, H.; Ueda, M.; Fujii, K.; Nishimura, A.; Naito, T. J. Org. Chem. 2003, 68, 5618-5626. Ueda, M.; Miyabe, H.; Nishimura, A.; Miyata, O.; Takemoto, Y.; Naito, T. Org. Lett. 2003, 5, 3835-3838.
159. For cyclizations of C=N acceptors initiated by intermolecular addition of alkyl radicals, see: Miyabe, H.; Fujii, K.; Goto, T.; Naito, T. Org. Lett. 2000, 2, 4071-4074. Miyabe, H.; Ueda, M.; Fujii, K.; Nishimura, A.; Naito, T. J. Org. Chem. 2003, 68, 5618-5626. Ueda, M.; Miyabe, H.; Nishimura, A.; Miyata, O.; Takemoto, Y.; Naito, T. Org. Lett. 2003, 5, 3835-3838.
160. For cyclizations of C=N acceptors initiated by intermolecular addition of alkyl radicals, see: Miyabe, H.; Fujii, K.; Goto, T.; Naito, T. Org. Lett. 2000, 2, 4071-4074. Miyabe, H.; Ueda, M.; Fujii, K.; Nishimura, A.; Naito, T. J. Org. Chem. 2003, 68, 5618-5626. Ueda, M.; Miyabe, H.; Nishimura, A.; Miyata, O.; Takemoto, Y.; Naito, T. Org. Lett. 2003, 5, 3835-3838.
161. This exploits a vinylsilane as a source of a tethered radical. Previously, intramolecular trapping of various cyclic radicals with a vinylsilane as a tethered radical acceptor has been reported by Matsuda et al. For examples, see: Kodama, T.; Shuto, S.; Nomura, M.; Matsuda, A. Chem. Eur. J. 2001, 7, 2332-2340. Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557 and references therein.
162. This exploits a vinylsilane as a source of a tethered radical. Previously, intramolecular trapping of various cyclic radicals with a vinylsilane as a tethered radical acceptor has been reported by Matsuda et al. For examples, see: Kodama, T.; Shuto, S.; Nomura, M.; Matsuda, A. Chem. Eur. J. 2001, 7, 2332-2340. Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557 and references therein.
163. 2-induced vinylsilane addition to an acyliminium ion has been reported. Hioki, H.; Izawa, T.; Yoshizuka, M.; Kunitake, R.; Ito, S. Tetrahedron Lett. 1995, 36, 2289-2292.
164. For a similar fluorodesilylative β-elimination of a β-phenylseleno group, see: Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153-7157.
165. In this experiment, cyclic hemiaminal 25 was also formed in low yield.
166. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99-102, and references therein. See also: Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343. Chandrasekhar, S.; Raza, A.; Takhi, M. Tetrahedron: Asymmetry 2001 13, 423-428. Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209-1212. Sabat, M.; Johnson, C. R. Org. Lett. 2000, 2, 1089-1092. Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187-3191. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653-2659.
167. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99-102, and references therein. See also: Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343. Chandrasekhar, S.; Raza, A.; Takhi, M. Tetrahedron: Asymmetry 2001 13, 423-428. Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209-1212. Sabat, M.; Johnson, C. R. Org. Lett. 2000, 2, 1089-1092. Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187-3191. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653-2659.
168. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99-102, and references therein. See also: Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343. Chandrasekhar, S.; Raza, A.; Takhi, M. Tetrahedron: Asymmetry 2001 13, 423-428. Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209-1212. Sabat, M.; Johnson, C. R. Org. Lett. 2000, 2, 1089-1092. Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187-3191. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653-2659.
169. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99-102, and references therein. See also: Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343. Chandrasekhar, S.; Raza, A.; Takhi, M. Tetrahedron: Asymmetry 2001 13, 423-428. Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209-1212. Sabat, M.; Johnson, C. R. Org. Lett. 2000, 2, 1089-1092. Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187-3191. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653-2659.
170. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99-102, and references therein. See also: Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343. Chandrasekhar, S.; Raza, A.; Takhi, M. Tetrahedron: Asymmetry 2001 13, 423-428. Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209-1212. Sabat, M.; Johnson, C. R. Org. Lett. 2000, 2, 1089-1092. Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187-3191. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653-2659.
171. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99-102, and references therein. See also: Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343. Chandrasekhar, S.; Raza, A.; Takhi, M. Tetrahedron: Asymmetry 2001 13, 423-428. Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209-1212. Sabat, M.; Johnson, C. R. Org. Lett. 2000, 2, 1089-1092. Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187-3191. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653-2659.
172. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99-102, and references therein. See also: Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343. Chandrasekhar, S.; Raza, A.; Takhi, M. Tetrahedron: Asymmetry 2001 13, 423-428. Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209-1212. Sabat, M.; Johnson, C. R. Org. Lett. 2000, 2, 1089-1092. Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187-3191. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653-2659.
173. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99-102, and references therein. See also: Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343. Chandrasekhar, S.; Raza, A.; Takhi, M. Tetrahedron: Asymmetry 2001 13, 423-428. Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209-1212. Sabat, M.; Johnson, C. R. Org. Lett. 2000, 2, 1089-1092. Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187-3191. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653-2659.
174. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99-102, and references therein. See also: Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343. Chandrasekhar, S.; Raza, A.; Takhi, M. Tetrahedron: Asymmetry 2001 13, 423-428. Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209-1212. Sabat, M.; Johnson, C. R. Org. Lett. 2000, 2, 1089-1092. Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187-3191. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653-2659.
175. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99-102, and references therein. See also: Collier, P. N.; Campbell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343. Chandrasekhar, S.; Raza, A.; Takhi, M. Tetrahedron: Asymmetry 2001 13, 423-428. Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209-1212. Sabat, M.; Johnson, C. R. Org. Lett. 2000, 2, 1089-1092. Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887-5890. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187-3191. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653-2659.
176. Hydrazones were obtained as single C=N bond isomers (>98: 2).
177. 1H NMR analysis of the cyclic silane intermediate did not give a clear indication of the diastereomer ratio.
178. The premature hydrogen abstraction process would be expected to be suppressed by slow addition of the thiophenol.
179. Pappo, R.; Allen, D. S.; Lemieux, R. U.; Johnson, W. S. J. Org. Chem. 1956, 21, 478-479.
180. The NOE enhancement was 10% at the internal vinyl hydrogen upon irradiation of the isopropyl methine; the inverse enhancement was 8% at the isopropyl methine.
181. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
182. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959-974.
183. Bushweller, C. H. In Conformational Behavior of Six-Membered Rings; Juaristi, E., Ed.; VCH: New York, 1995.
184. (a) Boat-axial conformations are considered to have negligible contributions to stereocontrol in 5-hexenyl radical cyclizations.10b
185. (b) Cyclohexane terminology for 5-hexenyl radical transition states is the current convention.10b
186. For kinetic data, see: Sturino, C. F.; Fallis, A. G. J. Org. Chem. 1994, 59, 6514-6516.
187. 1H NMR spectra.
188. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
189. 1H NMR analysis of the corresponding bis-Mosher esters (see the Supporting Information).
190. To our knowledge, this is the first example of asymmetric dihydroxylation in the presence of a hydrazone.
191. A mixture of syn and anti diols (dr 9:1) was employed. These inseparable isomers resulted from the 9:1 ratio of inseparable E- and Z-olefins used in the asymmetric dihydroxylation.
192. Mellor, J. M.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1984, 2927-2931. Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266-6267. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219-1222. Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447-7448. Martin, S. F.; Hom, R. K. Tetrahedron Lett. 1999, 40, 2887-2890. Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 2000, 56, 8673-8678. Deniau, E.; Enders, D. Tetrahedron 2001, 57, 2581-2588. Dahlen, A.; Hilmersson, G. Tetrahedron Lett. 2002, 43, 7197-7200.
193. Mellor, J. M.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1984, 2927-2931. Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266-6267. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219-1222. Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447-7448. Martin, S. F.; Hom, R. K. Tetrahedron Lett. 1999, 40, 2887-2890. Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 2000, 56, 8673-8678. Deniau, E.; Enders, D. Tetrahedron 2001, 57, 2581-2588. Dahlen, A.; Hilmersson, G. Tetrahedron Lett. 2002, 43, 7197-7200.
194. Mellor, J. M.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1984, 2927-2931. Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266-6267. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219-1222. Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447-7448. Martin, S. F.; Hom, R. K. Tetrahedron Lett. 1999, 40, 2887-2890. Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 2000, 56, 8673-8678. Deniau, E.; Enders, D. Tetrahedron 2001, 57, 2581-2588. Dahlen, A.; Hilmersson, G. Tetrahedron Lett. 2002, 43, 7197-7200.
195. Mellor, J. M.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1984, 2927-2931. Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266-6267. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219-1222. Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447-7448. Martin, S. F.; Hom, R. K. Tetrahedron Lett. 1999, 40, 2887-2890. Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 2000, 56, 8673-8678. Deniau, E.; Enders, D. Tetrahedron 2001, 57, 2581-2588. Dahlen, A.; Hilmersson, G. Tetrahedron Lett. 2002, 43, 7197-7200.
196. Mellor, J. M.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1984, 2927-2931. Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266-6267. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219-1222. Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447-7448. Martin, S. F.; Hom, R. K. Tetrahedron Lett. 1999, 40, 2887-2890. Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 2000, 56, 8673-8678. Deniau, E.; Enders, D. Tetrahedron 2001, 57, 2581-2588. Dahlen, A.; Hilmersson, G. Tetrahedron Lett. 2002, 43, 7197-7200.
197. Mellor, J. M.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1984, 2927-2931. Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266-6267. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219-1222. Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447-7448. Martin, S. F.; Hom, R. K. Tetrahedron Lett. 1999, 40, 2887-2890. Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 2000, 56, 8673-8678. Deniau, E.; Enders, D. Tetrahedron 2001, 57, 2581-2588. Dahlen, A.; Hilmersson, G. Tetrahedron Lett. 2002, 43, 7197-7200.
198. Mellor, J. M.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1984, 2927-2931. Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266-6267. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219-1222. Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447-7448. Martin, S. F.; Hom, R. K. Tetrahedron Lett. 1999, 40, 2887-2890. Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 2000, 56, 8673-8678. Deniau, E.; Enders, D. Tetrahedron 2001, 57, 2581-2588. Dahlen, A.; Hilmersson, G. Tetrahedron Lett. 2002, 43, 7197-7200.
199. Mellor, J. M.; Smith, N. M. J. Chem. Soc., Perkin Trans. 1 1984, 2927-2931. Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266-6267. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219-1222. Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447-7448. Martin, S. F.; Hom, R. K. Tetrahedron Lett. 1999, 40, 2887-2890. Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 2000, 56, 8673-8678. Deniau, E.; Enders, D. Tetrahedron 2001, 57, 2581-2588. Dahlen, A.; Hilmersson, G. Tetrahedron Lett. 2002, 43, 7197-7200.
200. A general statement describing materials and methods is provided in the Supporting Information.
201. Note that the theoretical yield is based on the portions of crude material used for each step.
202. For preparation of this compound, see the Supporting Information.