New Efficient Organic Activators for Highly Enantioselective Reduction of Aromatic Ketones by Trichlorosilane

Yoshihiro Matsumura,* Kanako Ogura, Yoshimi Kouchi, Fumiaki Iwasaki,† and Osamu Onomura
Graduate School of Biomedical Sciences, Nagasaki University,Bunkyo-machi, Nagasaki 8528521, Japan
Org. Lett., 2006, 8 (17), pp 3789–3792
DOI: 10.1021/ol0613822
Publication Date (Web): July 21, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Tsukuba Research Laboratory, Tokuyama Corporation, 40 Wadai, Tsukuba, 300-4247, Japan.

, matumura@net.nagasaki-u.ac.jp

Abstract

Abstract Image

Aryl ketones were reduced to the corresponding alcohols with excellent enantioselectivity (up to 99.7% ee) by Cl3SiH in the presence of a catalytic amount of N-formyl-α‘-(2,4,6-triethylphenyl)-l-proline as an activator. Both carboxyl group at the α-position of the activator and 2,4,6-triethylphenyl group at the α‘-position were critical for the high enantioselectivity.

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History

  • Published In Issue August 17, 2006
  • Received June 6, 2006

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