Highly stereoselective intermolecular radical addition to aldehyde hydrazones from a chiral 3-amino-2-oxazolidinone [16]

Journal of the American Chemical Society

Volumn 122, Issue 34, 2000, Pages 8329-8330

  Friestad, Gregory K ^a   Qin, Jun ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; ALDEHYDE; AMINE; HYDRAZONE DERIVATIVE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; LETTER; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0001651037     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja002173u     Document Type: Letter

References (52)

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2. Reviews: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Bloch, R. Chem. Rev. 1998, 98, 1407. (d) Enders, D.; Reinhold; U. Tetrahedron Asymmetry 1997, 8, 1895. (e) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
3. Reviews: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Bloch, R. Chem. Rev. 1998, 98, 1407. (d) Enders, D.; Reinhold; U. Tetrahedron Asymmetry 1997, 8, 1895. (e) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
4. Reviews: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Bloch, R. Chem. Rev. 1998, 98, 1407. (d) Enders, D.; Reinhold; U. Tetrahedron Asymmetry 1997, 8, 1895. (e) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
5. Reviews: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13. (c) Bloch, R. Chem. Rev. 1998, 98, 1407. (d) Enders, D.; Reinhold; U. Tetrahedron Asymmetry 1997, 8, 1895. (e) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
6. Aza-enolization of imines with Grignard reagents: Stork, G.; Dowd, S. R. J. Am. Chem. Soc. 1963, 85, 2178. Less basic organocerium reagents also exhibit aza-enolization: Enders, D.; Diez, E.; Fernandez, R.; Martin- Zamora, E.; Munoz, J. M.; Pappalardo, R. R.; Lassaleta, J. M. J. Org. Chem. 1999, 64, 6329.
7. Aza-enolization of imines with Grignard reagents: Stork, G.; Dowd, S. R. J. Am. Chem. Soc. 1963, 85, 2178. Less basic organocerium reagents also exhibit aza-enolization: Enders, D.; Diez, E.; Fernandez, R.; Martin-Zamora, E.; Munoz, J. M.; Pappalardo, R. R.; Lassaleta, J. M. J. Org. Chem. 1999, 64, 6329.
8. For selected recent examples, 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. (b) Mannich reactions: 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. (c) Allylation: Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. (d) Imino-ene reaction: Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yamanaka, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 159.
9. For selected recent examples, 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. (b) Mannich reactions: 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. (c) Allylation: Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. (d) Imino-ene reaction: Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yamanaka, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 159.
10. For selected recent examples, 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. (b) Mannich reactions: 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. (c) Allylation: Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. (d) Imino-ene reaction: Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yamanaka, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 159.
11. For selected recent examples, 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. (b) Mannich reactions: 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. (c) Allylation: Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. (d) Imino-ene reaction: Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yamanaka, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 159.
12. For selected recent examples, 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. (b) Mannich reactions: 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. (c) Allylation: Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. (d) Imino-ene reaction: Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yamanaka, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 159.
13. For selected recent examples, 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. (b) Mannich reactions: 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. (c) Allylation: Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. (d) Imino-ene reaction: Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yamanaka, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 159.
14. For selected recent examples, 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. (b) Mannich reactions: 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. (c) Allylation: Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. (d) Imino-ene reaction: Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yamanaka, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 159.
15. For selected recent examples, 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. (b) Mannich reactions: 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. (c) Allylation: Kobayashi, S.; Hirabayashi, R. J. Am. Chem. Soc. 1999, 121, 6942. (d) Imino-ene reaction: Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. Yamanaka, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 159.
16. (a) Review of radical cyclizations involving nitrogen: Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
17. (b) General reviews of radical reactions in organic synthesis: 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.
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20. For representative nonstereoselective intermolecular radical additions to C=N, see: Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631. Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. Kim, S.; Yoon, J.-Y. J. Am. Chem. Soc. 1997, 119, 5982. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189. Miyabe, H.; Ueda, M.; Yoshioka, N.; Yamakawa, K.; Naito, T. Tetrahedron 2000, 56, 2413.
21. For representative nonstereoselective intermolecular radical additions to C=N, see: Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631. Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. Kim, S.; Yoon, J.-Y. J. Am. Chem. Soc. 1997, 119, 5982. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189. Miyabe, H.; Ueda, M.; Yoshioka, N.; Yamakawa, K.; Naito, T. Tetrahedron 2000, 56, 2413.
22. For representative nonstereoselective intermolecular radical additions to C=N, see: Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631. Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. Kim, S.; Yoon, J.-Y. J. Am. Chem. Soc. 1997, 119, 5982. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189. Miyabe, H.; Ueda, M.; Yoshioka, N.; Yamakawa, K.; Naito, T. Tetrahedron 2000, 56, 2413.
23. For representative nonstereoselective intermolecular radical additions to C=N, see: Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631. Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. Kim, S.; Yoon, J.-Y. J. Am. Chem. Soc. 1997, 119, 5982. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189. Miyabe, H.; Ueda, M.; Yoshioka, N.; Yamakawa, K.; Naito, T. Tetrahedron 2000, 56, 2413.
24. For representative nonstereoselective intermolecular radical additions to C=N, see: Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631. Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. Kim, S.; Yoon, J.-Y. J. Am. Chem. Soc. 1997, 119, 5982. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189. Miyabe, H.; Ueda, M.; Yoshioka, N.; Yamakawa, K.; Naito, T. Tetrahedron 2000, 56, 2413.
25. For representative nonstereoselective intermolecular radical additions to C=N, see: Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631. Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. Kim, S.; Yoon, J.-Y. J. Am. Chem. Soc. 1997, 119, 5982. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189. Miyabe, H.; Ueda, M.; Yoshioka, N.; Yamakawa, K.; Naito, T. Tetrahedron 2000, 56, 2413.
26. For representative nonstereoselective intermolecular radical additions to C=N, see: Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631. Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. Kim, S.; Yoon, J.-Y. J. Am. Chem. Soc. 1997, 119, 5982. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189. Miyabe, H.; Ueda, M.; Yoshioka, N.; Yamakawa, K.; Naito, T. Tetrahedron 2000, 56, 2413.
27. For representative nonstereoselective intermolecular radical additions to C=N, see: Hart, D. J.; Seely, F. L. J. Am. Chem. Soc. 1988, 110, 1631. Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. Kim, S.; Yoon, J.-Y. J. Am. Chem. Soc. 1997, 119, 5982. Miyabe, H.; Shibata, R.; Ushiro, C.; Naito, T. Tetrahedron Lett. 1998, 39, 631. Miyabe, H.; Shibata, R.; Sangawa, M.; Ushiro, C.; Naito, T. Tetrahedron 1998, 54, 11431. Bertrand, M. P.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189. Miyabe, H.; Ueda, M.; Yoshioka, N.; Yamakawa, K.; Naito, T. Tetrahedron 2000, 56, 2413.
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49. 2) of N-acylhydrazones proved to be generally efficient; from appropriate ketone N-acylhydrazones, both diastereomers of 9c-f and 10c-f were acquired for characterization purposes (see Supporting Information).
50. 7 Preliminary experiments with 8 gave 1 as the major product (57% yield).
51. 2CuLi followed by interchange of the carbamate to benzamide. (b) Benzoylation of 10f (81% yield) as indicated in Scheme 2 gave material suitable for X-ray crystallography (see Supporting Information).
52. 12b