摘要：

A series of chiral pyrrolidinylmethanols were synthesized from (S)-proline. Optically active secondary alcohols (R and S enantiomers, respectively) in up to 100% enantiomeric excess (ee) were obtained in high yields from the enantioselective addition of dialkylzincs to aldehydes catalyzed by 2-5 mol % of chiral pyrrolidinylmethanols. The sense of the asymmetric induction and the degrees of enantioselectivities were highly dependent on the structure of the catalysts. (+)-DPMPM (3, tertiary amino tertiary alcohol) catalyzed the reaction of aryl, α,β-unsaturated, and aliphatic aldehydes to afford (S) alcohols in high ee's. When the lithium salt of 3 was employed as catalyst in the reactions of aryl and α,β-unsaturated aldehydes, the ee's of (S) alcohols reached 100%. On the other hand, (-)-erythro-PNPM (10, tertiary amino secondary alcohol) afforded (R) alcohols in high ee (100% ee). The steric course of the reaction is discussed.

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