Diastereoselective vinyl addition to chiral hydrazones via tandem thiyl radical addition and silicon-tethered cyclization

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4237-4240

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

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001487507     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0067991     Document Type: Article

References (92)

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11. Selected recent C-C bond construction approaches for synthesis of 1,2-amino alcohols: Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61, 2677. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219.
12. Selected recent C-C bond construction approaches for synthesis of 1,2-amino alcohols: Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61, 2677. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219.
13. Selected recent C-C bond construction approaches for synthesis of 1,2-amino alcohols: Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61, 2677. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219.
14. Selected recent C-C bond construction approaches for synthesis of 1,2-amino alcohols: Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61, 2677. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219.
15. Selected recent C-C bond construction approaches for synthesis of 1,2-amino alcohols: Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61, 2677. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219.
16. Selected recent C-C bond construction approaches for synthesis of 1,2-amino alcohols: Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61, 2677. Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219.
17. Wong, C.-H.; Hendrix, M.; Manning, D. D.; Rosenblum, C.; Greenberg, W. A. J. Am. Chem. Soc. 1998, 120, 8319 and references therein.
18. Alkene oxidation methods demand isomerically pure alkenes, which can in turn require nontrivial syntheses and/or separations.
19. Representative examples: Barrett, A. G. M.; Beall, J. C.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Salter, M. M. J. Org. Chem. 2000, 65, 6508. Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. Inaba, T.; Yamada, Y.; Abe, H.; Sagawa, S.; Cho, H. J. Org. Chem. 2000, 65, 1623. Boger, D. L.; Ledeboer, M. W.; Kume, M. J. Am. Chem. Soc. 1999, 121, 1098. Ghosh, A. K.; Wang, Y. J. Org. Chem. 1999, 64, 2789.
20. Representative examples: Barrett, A. G. M.; Beall, J. C.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Salter, M. M. J. Org. Chem. 2000, 65, 6508. Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. Inaba, T.; Yamada, Y.; Abe, H.; Sagawa, S.; Cho, H. J. Org. Chem. 2000, 65, 1623. Boger, D. L.; Ledeboer, M. W.; Kume, M. J. Am. Chem. Soc. 1999, 121, 1098. Ghosh, A. K.; Wang, Y. J. Org. Chem. 1999, 64, 2789.
21. Representative examples: Barrett, A. G. M.; Beall, J. C.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Salter, M. M. J. Org. Chem. 2000, 65, 6508. Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. Inaba, T.; Yamada, Y.; Abe, H.; Sagawa, S.; Cho, H. J. Org. Chem. 2000, 65, 1623. Boger, D. L.; Ledeboer, M. W.; Kume, M. J. Am. Chem. Soc. 1999, 121, 1098. Ghosh, A. K.; Wang, Y. J. Org. Chem. 1999, 64, 2789.
22. Representative examples: Barrett, A. G. M.; Beall, J. C.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Salter, M. M. J. Org. Chem. 2000, 65, 6508. Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. Inaba, T.; Yamada, Y.; Abe, H.; Sagawa, S.; Cho, H. J. Org. Chem. 2000, 65, 1623. Boger, D. L.; Ledeboer, M. W.; Kume, M. J. Am. Chem. Soc. 1999, 121, 1098. Ghosh, A. K.; Wang, Y. J. Org. Chem. 1999, 64, 2789.
23. Representative examples: Barrett, A. G. M.; Beall, J. C.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Salter, M. M. J. Org. Chem. 2000, 65, 6508. Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. Inaba, T.; Yamada, Y.; Abe, H.; Sagawa, S.; Cho, H. J. Org. Chem. 2000, 65, 1623. Boger, D. L.; Ledeboer, M. W.; Kume, M. J. Am. Chem. Soc. 1999, 121, 1098. Ghosh, A. K.; Wang, Y. J. Org. Chem. 1999, 64, 2789.
24. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Denmark, S. E.; Stiff, C. M. J. Org. Chem. 2000, 65, 5875. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
25. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Denmark, S. E.; Stiff, C. M. J. Org. Chem. 2000, 65, 5875. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
26. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Denmark, S. E.; Stiff, C. M. J. Org. Chem. 2000, 65, 5875. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
27. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Denmark, S. E.; Stiff, C. M. J. Org. Chem. 2000, 65, 5875. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
28. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Denmark, S. E.; Stiff, C. M. J. Org. Chem. 2000, 65, 5875. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
29. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Denmark, S. E.; Stiff, C. M. J. Org. Chem. 2000, 65, 5875. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
30. Reviews: Bloch, R. Chem. Rev. 1998, 98, 1407. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. Selected recent examples: Denmark, S. E.; Stiff, C. M. J. Org. Chem. 2000, 65, 5875. Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
31. (a) Stork, G.; Dowd, S. R. J. Am. Chem. Soc. 1963, 85, 2178.
32. (b) Even organocerium reagents, considered relatively nonbasic nucleophiles, can promote aza-enolization of hydrazones. Enders, D.; Diez, E.; Fernandez, R.; Martin-Zamora, E.; Munoz, J. M.; Pappalardo, R. R.; Lassaletta, J. M. J. Org. Chem. 1999, 64, 6329.
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35. The goal of mild, stereoselective C-C bond constructions with imino derivatives has generated significant research activity. For selected asymmetric approaches, see (a) Strecker reactions: Porter, J. R.; Wirschun, W. G.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 2657. Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762. Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157.
36. The goal of mild, stereoselective C-C bond constructions with imino derivatives has generated significant research activity. For selected asymmetric approaches, see (a) Strecker reactions: Porter, J. R.; Wirschun, W. G.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 2657. Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762. Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157.
37. The goal of mild, stereoselective C-C bond constructions with imino derivatives has generated significant research activity. For selected asymmetric approaches, see (a) Strecker reactions: Porter, J. R.; Wirschun, W. G.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 2657. Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762. Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157.
38. (b) Mannich reactions: Saito, S.; Hatanaka, K.; Yamamoto, H. Org. Lett. 2000, 2, 1891. Miura, K.; Tamaki, K.; Nakagawa, T.; Hosomi, A. Angew. Chem., Int. Ed. 2000, 39, 1958. Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450. Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168.
39. (b) Mannich reactions: Saito, S.; Hatanaka, K.; Yamamoto, H. Org. Lett. 2000, 2, 1891. Miura, K.; Tamaki, K.; Nakagawa, T.; Hosomi, A. Angew. Chem., Int. Ed. 2000, 39, 1958. Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450. Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168.
40. (b) Mannich reactions: Saito, S.; Hatanaka, K.; Yamamoto, H. Org. Lett. 2000, 2, 1891. Miura, K.; Tamaki, K.; Nakagawa, T.; Hosomi, A. Angew. Chem., Int. Ed. 2000, 39, 1958. Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450. Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168.
41. (b) Mannich reactions: Saito, S.; Hatanaka, K.; Yamamoto, H. Org. Lett. 2000, 2, 1891. Miura, K.; Tamaki, K.; Nakagawa, T.; Hosomi, A. Angew. Chem., Int. Ed. 2000, 39, 1958. Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450. Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168.
42. (c) Organostannane additions: Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976. Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242.
43. (c) Organostannane additions: Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976. Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242.
44. (c) Organostannane additions: Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976. Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242.
45. (c) Organostannane additions: Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976. Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1999, 64, 4844. Nakamura, H.; Nakamura, K.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 4242.
46. (d) Imino-ene reactions: Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006.
47. (e) Organotitanium additions: Teng, X.; Takayama, Y.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 11916.
48. (f) Nitrone cycloadditions: Ishikawa, T.; Kudo, T.; Shigemori, K.; Saito, S. J. Am. Chem. Soc. 2000, 122, 7633. Denmark, S. E.; Hurd, A. R. J. Org. Chem. 2000, 65, 2875.
49. (f) Nitrone cycloadditions: Ishikawa, T.; Kudo, T.; Shigemori, K.; Saito, S. J. Am. Chem. Soc. 2000, 122, 7633. Denmark, S. E.; Hurd, A. R. J. Org. Chem. 2000, 65, 2875.
50. Recent reviews of stereocontrol in radical reactions: Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: New York, 1995. Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562. General reviews of radical reactions in organic synthesis: Hart, D. J. Science 1984, 223, 883. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
51. Recent reviews of stereocontrol in radical reactions: Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: New York, 1995. Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562. General reviews of radical reactions in organic synthesis: Hart, D. J. Science 1984, 223, 883. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
52. Recent reviews of stereocontrol in radical reactions: Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: New York, 1995. Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562. General reviews of radical reactions in organic synthesis: Hart, D. J. Science 1984, 223, 883. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
53. Recent reviews of stereocontrol in radical reactions: Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: New York, 1995. Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562. General reviews of radical reactions in organic synthesis: Hart, D. J. Science 1984, 223, 883. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
54. Recent reviews of stereocontrol in radical reactions: Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: New York, 1995. Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562. General reviews of radical reactions in organic synthesis: Hart, D. J. Science 1984, 223, 883. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
55. Recent reviews of stereocontrol in radical reactions: Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: New York, 1995. Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562. General reviews of radical reactions in organic synthesis: Hart, D. J. Science 1984, 223, 883. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
56. Recent reviews of stereocontrol in radical reactions: Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines, and Synthetic Applications; VCH: New York, 1995. Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163. Renaud, P.; Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562. General reviews of radical reactions in organic synthesis: Hart, D. J. Science 1984, 223, 883. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986. Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
57. Review of radical cyclizations to C=N acceptors: Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
58. Friestad, G. K.; Qin, J. J. Am. Chem. Soc. 2000, 122, 8329.
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65. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500. Reviews of silicon-tethered reactions: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253.
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67. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500. Reviews of silicon-tethered reactions: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253.
68. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500. Reviews of silicon-tethered reactions: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253.
69. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298. Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500. Reviews of silicon-tethered reactions: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253.
70. Friestad, G. K. Org. Lett. 1999, 1, 1499.
71. Review: Naito, T. Heterocycles 1999, 50, 505. Recent examples involving C=N bonds: Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749.
72. Review: Naito, T. Heterocycles 1999, 50, 505. Recent examples involving C=N bonds: Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749.
73. Review: Naito, T. Heterocycles 1999, 50, 505. Recent examples involving C=N bonds: Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749.
74. Review: Naito, T. Heterocycles 1999, 50, 505. Recent examples involving C=N bonds: Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749.
75. Review: Naito, T. Heterocycles 1999, 50, 505. Recent examples involving C=N bonds: Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749.
76. Review: Naito, T. Heterocycles 1999, 50, 505. Recent examples involving C=N bonds: Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 6199. Depature, M.; Diewok, J..; Grimaldi, J.; Hatem, J. Eur. J. Org. Chem. 2000, 275. Ryu, I.; Ogura, S.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515. Depature, M.; Siri, D.; Grimaldi, J.; Hatem, J.; Faure, R. Tetrahedron Lett. 1999, 40, 4547. Marco-Contelles, J.; Rodriguez, M. Tetrahedron Lett. 1998, 39, 6749.
77. 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. Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547 and references therein.
78. 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.
79. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99 and references therein. See also: Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653.
80. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99 and references therein. See also: Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653.
81. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99 and references therein. See also: Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653.
82. For selected alternative preparations and applications, see: Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99 and references therein. See also: Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887. Harris, M. C. J.; Jackson, M.; Lennon, I. C.; Ramsden, J. A.; Samuel, H. Tetrahedron Lett. 2000, 41, 3187. Monache, G. D.; Misiti, D.; Salvatore, P.; Zappia, G.; Pierini, M. Tetrahedron: Asymmetry 2000, 11, 2653.
83. 13C NMR, IR, MS) provided in the Supporting Information.
84. For a similar fluorodesilylative β-elimination of a β-phenylseleno group, see: Sugimoto, I.; Shuto, S.; Matsuda, A. J. Org. Chem. 1999, 64, 7153.
85. Hydrazones were obtained as single C=N bond isomers (>98:2).
86. Relative configuration of 5d was assigned by chemical correlation: Acetonide formation, Lemieux-Johnson oxidation, reduction, and acetonide equilibration led to known anti-2-hydrazino-1,3 diol acetonide i (see Supporting Information). (Equation presented)
87. Previous work established that epimerization of α-hydroxy hydrazones during a related sequence did not occur except when the anion-stabilizing phenyl aroup was present (i.e.,1e). See ref 18.
88. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
89. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925. Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
90. Cyclohexane terminology for 5-hexenyl radical transition states is the current convention, see ref 12.
91. We did not attempt to determine the relative configuration of the phenylthiomethyl substituent in 4; this stereogenic center is lost during the subsequent elimination.
92. For kinetic data, see: Sturino, C. F.; Fallis, A. G. J. Org. Chem. 1994, 59, 6514.