Enantioselective and Diastereoselective Catalysis of the Mukaiyama Aldol Reaction: Ene Mechanism in Titanium-Catalyzed Aldol Reactions of Silyl Enol Ethers

Journal of the American Chemical Society

Volumn 115, Issue 15, 1993, Pages 7039-7040

  Mikami, Koichi ^a   Matsukawa, Satoru ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542586711     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00068a098     Document Type: Article

References (35)

1. Paterson, I.; Goodman, J. M.; Lister, M. A.; Schumann, R. C.; McClure, C. K.; Norcross, R. D. Tetrahedron 1990, 46, 4663.
2. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984, Vol. 3; Chapter 2.
3. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
4. Masamune, S.; Choy, W.; Peterson, J.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1986, 24, 1.
5. Kiyooka, S.; Kaneko, Y.; Kume, K. Tetrahedron Lett. 1992, 33, 4927.
6. Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
7. Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041.
8. Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247.
9. Mukaiyama, T.; Kobayashi, S.; Sano, T. Tetrahedron 1990, 46, 4653.
10. Parmee, E. R.; Tempkin, O.; Masamune, S.; Abiko, A. J. Am. Chem. Soc. 1991, 113, 9365
11. Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405.
12. Mukaiyama, T. Org. React. 1982, 28, 203.
13. Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 818.
14. Mukaiyama, T.; Narasaka, K.; Banno, K. J. Am. Chem. Soc. 1974, 96, 7503.
15. Mukaiyama, T.; Banno, K.; Narasaka, K. Chem. Lett. 1973, 1011.
16. Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox, D. N. A. Tetrahedron 1992, 48, 5731.
17. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
18. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon: London, 1991; Vols. 2 and 5.
19. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476.
20. Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556.
21. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807.
22. Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255.
23. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986.
24. Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer: Berlin, 1983; Vol. 3, p 217.
25. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949; 1989, 111, 1940.
26. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
27. Silica gel: Merck kieselgel 60, 70–230.
28. Kusumi, T.; Ohtani, I.; Inouye, Y.; Kakisawa, H. Tetrahedron Lett. 1988, 29, 4731.
29. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370.
30. Dale, J. A.; Mosher, H.S. J. Am. Chem. Soc. 1973, 95, 512.
31. Snider, B. B.; Phillips, G. B. J. Org. Chem. 1983, 48, 2789.
32. Maruoka, K.; Concepcion, A. B.; Hirayama, N.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 7422.
33. Mikami, K.; Loh, T.-P.; Nakai, T. Tetrahedron Lett. 1988, 29, 6305.
34. Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248.
35. Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 37, 3899.