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Direct Asymmetric Aldol Reaction Catalyzed by Proline-Proline Dipeptide

Zongxuan Shen

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Abstract

Two dipeptides,H-(S)-Pro-(S)-Pro-OH(1) and H-(S)-Pro-(R)-Pro-OH(2),were prepared from(S)-and(R)-proline,and applied in direct asymmetric Aldol reaction.In both cases,the product had(S)-configuration,which was opposite to that obtained by(S)-proline catalysis.Low enantioselectivities(less than 21 %) were found.Data from the computational research could well explain the experimental results.

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What this paper is about

Two dipeptides,H-(S)-Pro-(S)-Pro-OH(1) and H-(S)-Pro-(R)-Pro-OH(2),were prepared from(S)-and(R)-proline,and applied in direct asymmetric Aldol reaction.In both cases,the product had(S)-configuration,which was opposite to that obtained by(S)-proline catalysis.Low enantioselectivities(less than 21 %) were found.Data from the computational research could well explain the experimental results.

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Available abstract

Two dipeptides,H-(S)-Pro-(S)-Pro-OH(1) and H-(S)-Pro-(R)-Pro-OH(2),were prepared from(S)-and(R)-proline,and applied in direct asymmetric Aldol reaction.In both cases,the product had(S)-configuration,which was opposite to that obtained by(S)-proline catalysis.Low enantioselectivities(less than 21 %) were found.Data from the computational research could well explain the experimental results.

Key concepts: Aldol reaction, Proline, Dipeptide, Chemistry, Catalysis, Organocatalysis, Stereochemistry, Combinatorial chemistry

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