Highly Enantioselective Cr(salen)-catalyzed Reaction of 2-(Trimethylsilyloxy)furan and Aldehydes. Effect of Alcohol on Enantioselectivity

Chemistry Letters

Volumn 32, Issue 10, 2003, Pages 974-975

  Onitsuka, Satoaki ^a   Matsuoka, Yuko ^a   Irie, Ryo ^a   Katsuki, Tsutomu ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

2 (TRIMETHYLSILYLOXY)FURAN; ALCOHOL; ALDEHYDE DERIVATIVE; CHROMIUM DERIVATIVE; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY;

EID: 0346162171     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.974     Document Type: Article

References (22)

1. a) M. Asaoka, N. Sugimura, and H. Takei, Bull. Chem. Soc. Jpn., 52, 1953 (1979).
2. b) C. W. Jefford, D. Jaggi, and J. Boukouvalas, Tetrahedron Lett., 28, 4037 (1987).
3. a) D. W. Brown, M. M. Campbell, A. P. Taylor, and X. Zhang, Tetrahedron Lett., 28, 985 (1987).
4. b) G. Casiraghi, L. Colombo, G. Rassu, and P. Spanu, Tetrahedron Lett., 30, 5325 (1989).
5. c) T. Bauer, Tetrahedron: Asymmetry, 7, 981 (1996).
6. T. Fukuyama and L. Yang, Tetrahedron Lett., 27, 6299 (1986).
7. M. A. Brimble, M. T. Brimble, and J. J. Gibson, J. Chem. Soc., Perkin Trans. 1, 1989, 179.
8. H. Kitajima and T. Katsuki, Synlett, 1997, 568.
9. D. A. Evans, C. S. Burgey, M. C. Kozlowski, and S. W. Tregay, J. Am. Chem. Soc., 121, 686 (1999).
10. M. Szlosek, X. Franck, B. Figadére, and A. Cavé, J. Org. Chem., 63, 5169 (1998).
11. M. Szlosek and B. Figadére, Angew. Chem., Int. Ed. Engl., 39, 1799 (2000).
12. Metallosalens possessing a binaphthyl unit are referred to as second-generation metallosalens: Y. N. Ito and T. Katsuki, Bull. Chem. Soc. Jpn., 72, 603 (1999).
13. Y. Matsuoka, R. Irie, and T. Katsuki, Chem. Lett., 32, 584 (2003).
14. E. M. Carreira, in "Comprehensive Asymmetric Catalysis III," ed. by E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Springer, Berlin (1999), Vol. 29.1, p 997.
15. For the previous discussions of water effect on asymmetric Mukaiyama aldol reactions, see: a) M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995). b) O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998). c) S. Kobayashi, S. Nagayama, and T. Busujima, Tetrahedron, 55, 8739 (1999). d) Y. Yamashita, H. Ishitani, H. Shimizu, and S. Kobayashi, J. Am. Chem. Soc., 124, 3292 (2002).
16. For the previous discussions of water effect on asymmetric Mukaiyama aldol reactions, see: a) M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995). b) O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998). c) S. Kobayashi, S. Nagayama, and T. Busujima, Tetrahedron, 55, 8739 (1999). d) Y. Yamashita, H. Ishitani, H. Shimizu, and S. Kobayashi, J. Am. Chem. Soc., 124, 3292 (2002).
17. For the previous discussions of water effect on asymmetric Mukaiyama aldol reactions, see: a) M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995). b) O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998). c) S. Kobayashi, S. Nagayama, and T. Busujima, Tetrahedron, 55, 8739 (1999). d) Y. Yamashita, H. Ishitani, H. Shimizu, and S. Kobayashi, J. Am. Chem. Soc., 124, 3292 (2002).
18. For the previous discussions of water effect on asymmetric Mukaiyama aldol reactions, see: a) M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995). b) O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998). c) S. Kobayashi, S. Nagayama, and T. Busujima, Tetrahedron, 55, 8739 (1999). d) Y. Yamashita, H. Ishitani, H. Shimizu, and S. Kobayashi, J. Am. Chem. Soc., 124, 3292 (2002).
19. In the reviewing process of our previous communication (Ref. 10), the reviewers gave useful comments on the reaction mechanism, which helped to promote the present study. We are grateful for the reviewer's comments.
20. For the examples of additive effect of alcohol in asymmetric addition reaction of silyl enol ethers, see: Refs. 5, 12d, and D. A. Evans, K. A. Scheidt, J. N. Johnston, and M. C. Willis, J. Am. Chem. Soc., 123, 4480 (2001) and references cited therein.
21. The O-trimethylsilylated product was obtained, instead of the desired δ-hydroxy butenolide.
22. 1H NMR (400 MHz) analysis. The enantiomeric excess of the resulting butenolides was determined by HPLC analysis using chiral column (DAICEL CHIRALPAK AS-H, hexane/isopropanol = 9/1).