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Stereoselective reactions 2. asymmetric synthesis of beta substituted aldehydes by michael reaction using chiral alpha beta unsaturated aldimines



Stereoselective reactions 2. asymmetric synthesis of beta substituted aldehydes by michael reaction using chiral alpha beta unsaturated aldimines



Chemical and Pharmaceutical Bulletin 27(10): 2437-2441



The Michael reaction of diethyl malonate with chiral .alpha.,.beta.-unsaturated aldimines, prepared from crotonaldehyde and optically active .alpha.-amino acid tert-butyl esters, gave the corresponding .beta.-substituted aldehydes in reasonably high optical yields after hydrolysis. A proposed stereochemical mechanism of the reaction is presented.

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