Novel camphor-derived chiral auxiliaries: Significant solvent and additive effects on asymmetric reduction of chiral α-keto esters

Journal of Organic Chemistry

Volumn 64, Issue 19, 1999, Pages 6993-6998

  Chu, Ying Yuan ^a,b   Yu, Chia Sheng ^a,b   Chen, Chiou Juy ^a,b   Yang, Kung Shuo ^a   Lain, Jung Chaing ^a   Lin, Chun Hui ^a   Chen, Kwunmin ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

^b CHAOYANG UNIVERSITY OF TECHNOLOGY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; MOLECULAR MODEL; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0033578844     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9902188     Document Type: Article

References (27)

1. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press: New York, 1983; Chapter 2.
2. For recent references, see: (a) Whitesell, J. K.; Deyo, D.; Bhattacharya, A. J. Chem. Soc., Chem. Commun. 1983, 802.
3. (b) Solladie-Cavallo, A.; Bencheqroun, M. Tetrahedron: Asymmetry 1991, 2, 1165.
4. Akiyama, T.; Nishimoto, H.; Ozaki, S. Tetrahedron Lett. 1961, 32, 1335.
5. Xiang, Y. B.; Snow, K.; Belley, M. J. Org. Chem. 1993, 58, 993.
6. (e) Maitra, U.; Mathivanan, P. Tetrahedron: Asymmetry 1994, 5, 1171.
7. (f) Ghosh, A. K.; Chen, Y. Tetrahedron Lett. 1995, 36, 6811.
8. (g) Akiyama, T.; Nishimoto, H.; Kuwata, T.; Ozaki, S. Bull. Chem. Soc. Jpn. 1994, 67, 180.
9. (h) Soai, K.; Isoda, T.; Hasegawa, H.; Ishizaki, M. Chem. Lett. 1986, 1897.
10. Kawanami, Y.; Fujita, I.; Asahara, S.; Kasuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1989, 62, 3598.
11. (j) Kawanami, Y.; Fujita, I.; Taniguchi, Y.; Katsuki, T.; Yamaguchi, M. Chem. Lett. 1987, 2021.
12. (k) Solodin, I.; Goldberg, Y.; Zelcans, G.; Lukevics, E. J. Chem. Soc., Chem. Commun. 1990, 1321.
13. Chen, C.-J.; Chu, Y.-Y.; Liao, Y.-Y.; Tsai, Z.-H.; Wang, C.-C.; Chen, K. Tetrahedron Lett. 1999, 40, 1141.
14. Bartlett, P. D.; Knox, L. H. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 689.
15. Padwa, A.; Koehler, K. F. J. Chem. Soc. Chem. Commun., 1986, 789.
16. Mori, K.; Akao, H. Tetrahedron 1980, 36, 91.
17. Byun, S.; Kim, Y. H. Synth. Commun. 1995, 25, 1963.
18. Chenault, H. K.; Kim, M.-J.; Akiyama, A.; Miyazawa, T.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2608.
19. Solladié, G.; Demailly, G.; Greek, C. Tetrahedron Lett. 1985, 26, 435.
20. (a) Kobayashi, S.; Horibe, M. Tetrahedron 1996, 52, 7277.
21. (b) Alvarez-Ibarra, C.; Csáky, A. G.; Maroto, R.; Quiroga, M. L. J. Org. Chem. 1995, 60, 7934.
22. Meyer, L.; Poirier, J.-M.; Duhamel, P.; Duhamel, L. J. Org. Chem. 1998, 63, 8094.
23. Solladie, G.; Greek, C.; Demailly, G.; Solladie-Cavallo, A. Tetrahedron Lett. 1982, 23, 5047.
24. (e) Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098.
25. (f) Kobayashi, S.; Horibe, M.; Saito, Y. Tetrahedron 1994, 50, 9629.
26. (g) Kobayashi, S.; Horibe, M. J. Am. Chem. Soc. 1994, 116, 9805.
27. (h) Sibi, M.; Shay, J. J.; Liu, M.; Jasperse, C. P. J. Am. Chem. Soc. 1998, 120, 6615.