Lithium pyrrolidone catalyzed aldol reaction between aldehyde and trimethylsilyl enolate

Chemistry Letters

Volumn , Issue 8, 2002, Pages 858-859

  Fujisawa, Hidehiko ^a   Mukaiyama, Teruaki ^a  

^a KITASATO INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM PYRROLIDONE; PYRIDINE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; TEMPERATURE;

EID: 0037025489     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.858     Document Type: Article

References (21)

1. For reviews, see: S. G. Nelson, Tetrahedron: Asymmetry, 9, 357 (1998); R. Mahrwald, Chem. Rev., 99, 1095 (1999); T. D. Machajewski and C.-H. Wong, Angew. Chem., Int. Ed., 39, 1352 (2000).
2. For reviews, see: S. G. Nelson, Tetrahedron: Asymmetry, 9, 357 (1998); R. Mahrwald, Chem. Rev., 99, 1095 (1999); T. D. Machajewski and C.-H. Wong, Angew. Chem., Int. Ed., 39, 1352 (2000).
3. For reviews, see: S. G. Nelson, Tetrahedron: Asymmetry, 9, 357 (1998); R. Mahrwald, Chem. Rev., 99, 1095 (1999); T. D. Machajewski and C.-H. Wong, Angew. Chem., Int. Ed., 39, 1352 (2000).
4. T. Mukaiyama, K. Banno, and K. Narasaka, J. Am. Chem. Soc., 96, 7503 (1974).
5. G. Stork and P. F. Hudrlik, J. Am. Chem. Soc., 90, 4462 (1968); H. O. House, D. S. Crumrine, A. Y. Teranishi, and H. D. Olmstead, J. Am. Chem. Soc., 95, 3310 (1973); M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995); J. Krüger and E. M. Carreira, J. Am. Chem. Soc., 120, 837 (1998); O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998); H. Fujisawa, Y. Sasaki, and T. Mukaiyama, Chem. Lett., 2001, 190.
6. G. Stork and P. F. Hudrlik, J. Am. Chem. Soc., 90, 4462 (1968); H. O. House, D. S. Crumrine, A. Y. Teranishi, and H. D. Olmstead, J. Am. Chem. Soc., 95, 3310 (1973); M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995); J. Krüger and E. M. Carreira, J. Am. Chem. Soc., 120, 837 (1998); O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998); H. Fujisawa, Y. Sasaki, and T. Mukaiyama, Chem. Lett., 2001, 190.
7. G. Stork and P. F. Hudrlik, J. Am. Chem. Soc., 90, 4462 (1968); H. O. House, D. S. Crumrine, A. Y. Teranishi, and H. D. Olmstead, J. Am. Chem. Soc., 95, 3310 (1973); M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995); J. Krüger and E. M. Carreira, J. Am. Chem. Soc., 120, 837 (1998); O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998); H. Fujisawa, Y. Sasaki, and T. Mukaiyama, Chem. Lett., 2001, 190.
8. G. Stork and P. F. Hudrlik, J. Am. Chem. Soc., 90, 4462 (1968); H. O. House, D. S. Crumrine, A. Y. Teranishi, and H. D. Olmstead, J. Am. Chem. Soc., 95, 3310 (1973); M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995); J. Krüger and E. M. Carreira, J. Am. Chem. Soc., 120, 837 (1998); O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998); H. Fujisawa, Y. Sasaki, and T. Mukaiyama, Chem. Lett., 2001, 190.
9. G. Stork and P. F. Hudrlik, J. Am. Chem. Soc., 90, 4462 (1968); H. O. House, D. S. Crumrine, A. Y. Teranishi, and H. D. Olmstead, J. Am. Chem. Soc., 95, 3310 (1973); M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995); J. Krüger and E. M. Carreira, J. Am. Chem. Soc., 120, 837 (1998); O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998); H. Fujisawa, Y. Sasaki, and T. Mukaiyama, Chem. Lett., 2001, 190.
10. G. Stork and P. F. Hudrlik, J. Am. Chem. Soc., 90, 4462 (1968); H. O. House, D. S. Crumrine, A. Y. Teranishi, and H. D. Olmstead, J. Am. Chem. Soc., 95, 3310 (1973); M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995); J. Krüger and E. M. Carreira, J. Am. Chem. Soc., 120, 837 (1998); O. Fujimura, J. Am. Chem. Soc., 120, 10032 (1998); H. Fujisawa, Y. Sasaki, and T. Mukaiyama, Chem. Lett., 2001, 190.
11. R. Noyori, K. Yokoyama, J. Sakata, I. Kuwajima, E. Nakamura, and M. Shimizu, J. Am. Chem. Soc., 99, 1265 (1977); R. Noyori, I. Nishida, and J. Sakata, J. Am. Chem. Soc., 103, 2106 (1981).
12. R. Noyori, K. Yokoyama, J. Sakata, I. Kuwajima, E. Nakamura, and M. Shimizu, J. Am. Chem. Soc., 99, 1265 (1977); R. Noyori, I. Nishida, and J. Sakata, J. Am. Chem. Soc., 103, 2106 (1981).
13. S. Matsukawa, N. Okano, and T. Imamoto, Tetrahedron Lett., 41, 103 (2000).
14. A. G. Myers, S. E. Kephart, and H. Chen, J. Am. Chem. Soc., 114, 7922 (1992); S. E. Denmark, B. D. Griedel, D. M. Coe, and M. E. Schnute, J. Am. Chem. Soc., 116, 7026 (1994).
15. A. G. Myers, S. E. Kephart, and H. Chen, J. Am. Chem. Soc., 114, 7922 (1992); S. E. Denmark, B. D. Griedel, D. M. Coe, and M. E. Schnute, J. Am. Chem. Soc., 116, 7026 (1994).
16. Y. Génisson and L. Gorrichon, Tetrahedron Lett., 41, 4881 (2000).
17. S. E. Denmark and R. A. Stavenger, Acc. Chem. Res., 33, 432 (2000).
18. K. Miura, T. Nakagawa, and A. Hosomi, J. Am. Chem. Soc., 124, 536 (2002).
19. H. Fujisawa and T. Mukaiyama, Chem. Lett., 2002, 182.
20. F. G. Bordwell, Acc. Chem. Res., 21, 456 (1988); F. G. Bordwell, J. C. Branca, D. L. Hughes, and W. N. Olmstead, J. Org. Chem., 45, 3305 (1980).
21. F. G. Bordwell, Acc. Chem. Res., 21, 456 (1988); F. G. Bordwell, J. C. Branca, D. L. Hughes, and W. N. Olmstead, J. Org. Chem., 45, 3305 (1980).