Magnesium bromide diethyl etherate mediated highly diastereoselective aldol reaction between an aldehyde and a silyl enol ether

Chemistry Letters

Volumn , Issue 3, 2001, Pages 190-191

  Fujisawa, Hidehiko ^a   Sasaki, Yasuhiro ^a   Mukaiyama, Teruaki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035532076     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.190     Document Type: Article

References (20)

1. W. H. Pearson and M. C. Cheng, J. Org. Chem., 52, 3176 (1987); T. Mukaiyama, H. Uchiro, I. Shiina, and S. Kobayashi, Chem. Lett., 1990, 1019; T. Mukaiyama, I. Shiina, and S. Kobayashi, Chem. Lett., 1991, 1901; D. A. Evans and S. L. Bender, Tetrahedron Lett, 27, 799 (1986); T. K. Jones, S. G. Mills, R. A. Reamer, D. Askin, R. Desmond, R. P. Volante, and I. Shinkai, J. Am. Chem. Soc., 111, 1157 (1989).
2. W. H. Pearson and M. C. Cheng, J. Org. Chem., 52, 3176 (1987); T. Mukaiyama, H. Uchiro, I. Shiina, and S. Kobayashi, Chem. Lett., 1990, 1019; T. Mukaiyama, I. Shiina, and S. Kobayashi, Chem. Lett., 1991, 1901; D. A. Evans and S. L. Bender, Tetrahedron Lett, 27, 799 (1986); T. K. Jones, S. G. Mills, R. A. Reamer, D. Askin, R. Desmond, R. P. Volante, and I. Shinkai, J. Am. Chem. Soc., 111, 1157 (1989).
3. W. H. Pearson and M. C. Cheng, J. Org. Chem., 52, 3176 (1987); T. Mukaiyama, H. Uchiro, I. Shiina, and S. Kobayashi, Chem. Lett., 1990, 1019; T. Mukaiyama, I. Shiina, and S. Kobayashi, Chem. Lett., 1991, 1901; D. A. Evans and S. L. Bender, Tetrahedron Lett, 27, 799 (1986); T. K. Jones, S. G. Mills, R. A. Reamer, D. Askin, R. Desmond, R. P. Volante, and I. Shinkai, J. Am. Chem. Soc., 111, 1157 (1989).
4. W. H. Pearson and M. C. Cheng, J. Org. Chem., 52, 3176 (1987); T. Mukaiyama, H. Uchiro, I. Shiina, and S. Kobayashi, Chem. Lett., 1990, 1019; T. Mukaiyama, I. Shiina, and S. Kobayashi, Chem. Lett., 1991, 1901; D. A. Evans and S. L. Bender, Tetrahedron Lett, 27, 799 (1986); T. K. Jones, S. G. Mills, R. A. Reamer, D. Askin, R. Desmond, R. P. Volante, and I. Shinkai, J. Am. Chem. Soc., 111, 1157 (1989).
5. W. H. Pearson and M. C. Cheng, J. Org. Chem., 52, 3176 (1987); T. Mukaiyama, H. Uchiro, I. Shiina, and S. Kobayashi, Chem. Lett., 1990, 1019; T. Mukaiyama, I. Shiina, and S. Kobayashi, Chem. Lett., 1991, 1901; D. A. Evans and S. L. Bender, Tetrahedron Lett, 27, 799 (1986); T. K. Jones, S. G. Mills, R. A. Reamer, D. Askin, R. Desmond, R. P. Volante, and I. Shinkai, J. Am. Chem. Soc., 111, 1157 (1989).
6. I. Shiina, J. Shibata, Y. Imai, R. Ibuka, H. Fujisawa, I. Hachiya, and T. Mukaiyama, Chem. Lett., 1999, 1145.
7. 2 failed to promote this reaction.)
8. I. Kuwajima and E. Nakamura, Acc. Chem. Res., 18, 181 (1985); M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995).
9. I. Kuwajima and E. Nakamura, Acc. Chem. Res., 18, 181 (1985); M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995).
10. G. Stork and P. F. Hudrlik, J. Am. Chem. Soc., 90, 4464 (1968).
11. 1H NMR measurements. It was unable to observe directly the magnesium enolate formed from 1 probably because of aggregation of the formed magnesium enolate and their decomposition.
12. K. Takai and C. H. Heathcock, J. Org. Chem., 50, 3247 (1985); J. Uenishi, H. Tomozane, and M. Yamato, Tetrahedron Lett, 26, 3467 (1985); A. Bernardi, S. Cardani, L. Colombo, G. Poli, G. Schimperna, and C. Scolastico, J. Org. Chem., 52, 888 (1987).
13. K. Takai and C. H. Heathcock, J. Org. Chem., 50, 3247 (1985); J. Uenishi, H. Tomozane, and M. Yamato, Tetrahedron Lett, 26, 3467 (1985); A. Bernardi, S. Cardani, L. Colombo, G. Poli, G. Schimperna, and C. Scolastico, J. Org. Chem., 52, 888 (1987).
14. K. Takai and C. H. Heathcock, J. Org. Chem., 50, 3247 (1985); J. Uenishi, H. Tomozane, and M. Yamato, Tetrahedron Lett, 26, 3467 (1985); A. Bernardi, S. Cardani, L. Colombo, G. Poli, G. Schimperna, and C. Scolastico, J. Org. Chem., 52, 888 (1987).
15. S. Yamago, D. Machii, and E. Nakamura, J. Org. Chem., 56, 2098 (1991); Y. Li, M. N. Paddon-Row, and K. N. Houk, J. Org. Chem., 55, 481 (1990).
16. S. Yamago, D. Machii, and E. Nakamura, J. Org. Chem., 56, 2098 (1991); Y. Li, M. N. Paddon-Row, and K. N. Houk, J. Org. Chem., 55, 481 (1990).
17. M. M. Mader and J. C. Edel, J. Org. Chem., 63, 2761 (1998).
18. M. Terada, J. H. Gu, D. C. Deka, K. Mikami, and T. Nakai, Chem. Lett., 1992, 29.
19. C. H. Heathcock, S. K. Davidsen, K. T. Hug, and L. A. Flippin, J. Org. Chem., 51, 3027 (1986).
20. E. J. Corey, W. Li, and G. A. Reichard, J. Am. Chem. Soc., 120, 2330 (1998).