Abstract
A simple method is proposed for the synthesis of optically active indole-2-carbaldehydes via alkylation of 2-cyanoindole by optically active secondary alcohols and subsequent reduction of the cyano group to an aldehyde. Reaction of the aldehydes obtained with aromatic amines gave imines whose reaction with the Danishefsky diene was studied. The structure of the major diastereomer of (2R′)-1-phenyl-2-[1-((1R′)-1-phenylethyl)indol-2-yl]-1,2,3,4-tetrahydropyridine-4-one and minor diastereomer (2S)-2-[1-((1S)-2-methoxy-1-phenylethyl)indol-2-yl]-1-phenyl-1,2,3,4-tetrahydropyridine-4-one respectively were established by X-ray analysis.
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