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Enantioselective 1,4-addition of unmodified ketone catalyzed by a bimetallic Zn-Zn-linked-BINOL complex
N Kumagai1, S Matsunaga, M Shibasaki
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Organic Letters
|January 11, 2002
Abstract:
1,4-Addition (Michael addition) of 2-hydroxy-2'-methoxyacetophenone (2) to various alpha,beta-unsaturated ketones was efficiently promoted by a bimetallic Zn-Zn-linked-BINOL complex 3 with good yield (up to 90%) and excellent enantiomeric excess (up to 99% ee). The resulting 2-hydroxy-1,5-diketones were successfully converted to synthetically more versatile esters and amides. [reaction: see text]