Asymmetric azo-ene reactions using the chiral azo-enophile di-(-)- (1R,2S)-2-phenyl-1-cyclohexyl diazenedicarboxylate

Tetrahedron Asymmetry

Volumn 9, Issue 5, 1998, Pages 873-884

  Brimble, Margaret A ^a   Lee, Connie K Y ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; 2 PHENYL 1 CYCLOHEXYL DIAZENEDICARBOXYLATE; AMMONIA; AZO COMPOUND; CARBAMIC ACID DERIVATIVE; CYCLOPENTENE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; AZO ENE REACTION; CHIRALITY; DIASTEREOISOMER; HYDROLYSIS; OXIDATION; PRIORITY JOURNAL;

EID: 0032513140     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00034-2     Document Type: Article

References (34)

1. 1. (a) Kresze, G., Munsterer, H. J. Org. Chem., 1983, 48, 3561;
2. (b) Sharpless, K. B., Hori, T., Truesdale, L. K., Dietrich, C. L. J. Am. Chem. Soc. 1976, 98, 269;
3. (c) Singer, S. P., Sharpless, K. B. J. Org. Chem. 1978, 43, 1448.
4. 2. Tschaen, D. M., Turos, E., Weinreb, S. M. J. Org. Chem. 1984, 49, 5058.
5. 3. Keck, G. E., Webb, R. R., Yates, J. B. Tetrahedron 1981, 37, 4007.
6. 4. Deleris, G., Dunogues, J. M., Gadras, A. Tetrahedron 1988, 44, 4243.
7. 5. Whitesell, J. K., Yaser, H. K. J. Am. Chem. Soc. 1991, 113, 3526.
8. 6. For general reviews on the ene reaction see: (a) Hofmann, H. M. R. Angew. Chem. Int. Ed. Engl. 1969, 8, 556;
9. (b) Snider, B. B. 'Ene Reactions with Alkenes As Electrophiles'. In Comprehensive Organic Synthesis, ed. Trost, B. M.; Pergamon: Oxford, 1991, vol. 5, p. 1.
10. 7. (a) For a review of the carbonyl-ene reaction see: Snider, B. B. 'The Prins and Carbonyl-Ene Reactions'. In Comprehensive Organic Synthesis, ed. Trost, B. M.; Pergamon: Oxford, 1991, vol. 2, p. 527;
11. (b) Mikami, K., Shimizu, M. Chem. Rev. 1992, 92, 1021.
12. 8. For a review of the imino-ene reaction see: Borzilleri, R. M., Weinreb., S. M. Synthesis 1995, 347. 9.
13. For a review of Lewis acid catalysed ene reactions see: Snider, B. B. Acc. Chem. Res. 1980, 13, 426.
14. 10. For leading references see: (a) Mikami, K., Terada, M., Narisawa, S., Nakai, T. Synlett. 1992, 255-271;
15. (b) Mikami, K., Terada, M., Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949;
16. (c) Mikami, K., Terada, M. J. Chem. Soc., Chem. Commun. 1994, 833;
17. (d) Mikami, K., Yoshida, A., Matsumoto, Y. Tetrahedron Lett. 1996, 37, 8515.
18. 11. Corey, E. J., Barnes-Seeman, D., Lee, T. W., Goodman, S. N. Tetrahedron Lett. 1997, 38, 6513.
19. 12. (a) Whitesell, J. K. Acc. Chem. Res. 1985, 18, 280;
20. (b) Whitesell, J. K., Allen, D. E. J. Org. Chem. 1985, 50, 3025;
21. (b) Whitesell, J. K., Allen, D. E. J. Am. Chem. Soc. 1988, 110, 3585;
22. (c) Whitesell, J. K., Minton, M. A. J. Am. Chem. Soc. 1986, 108, 6802.
23. 13. Mikami, K., Kaneko, M., Yajima, T. Tetrahedron Lett. 1993, 34, 4841.
24. 14. Jezewski, A., Chajewska, K., Wielogorski, Z., Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 1741.
25. 15. (a) Harris, J. M., Bolessa, E. A., Mendonca, A. J., Feng, S.-C., Vederas, J. C. J. Chem. Soc., Perkin Trans 1 1995, 1945;
26. (b) Harris, J. M., Bolessa, E. A., Vederas, J. C. J. Chem. Soc., Perkin Trans 1 1995, 1951;
27. (c) Harris, J. M., McDonald, R., Vederas, J. C. J. Chem. Soc., Perkin Trans 1 1996, 2669.
28. 16. Brimble, M. A., Heathcock, C. H. J. Org. Chem. 1993, 55, 5261.
29. 17. Evans, D. A., Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452.
30. 18. Leblanc, Y., Zamboni, R., Bernstein, M. A. J. Org. Chem. 1991, 56, 1971.
31. 19. Brimble, M. A., Heathcock, C. H., Nobin, G. N. Tetrahedron: Asymmetry 1996, 7, 2007.
32. 20. Moriarty, M., Prakash, I., Penmasta, R. Synth. Commun. 1987, 17, 409.
33. 21. Starr, J. T., Rai, G. S., Dang, H., McNelis, B. J. Synth. Commun. 1997, 27, 3197.
34. 22. King, S. B., Sharpless, K. B. Tetrahedron Lett. 1994, 35, 5611.