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Enantioselective synthesis of anti-beta-substituted gamma,delta-unsaturated amino acids: a highly selective asymmetric thio-Claisen rearrangement.

ABSTRACT: A novel synthesis of optically active anti-beta-substituted gamma,delta-unsaturated amino acids via a thio-Claisen rearrangement has been achieved. A 2,5-diphenylpyrrolidine was used as a C2-symmetric chiral auxiliary to control the stereochemistry, giving good yields and excellent diastereoselectivities and enantioselectivities.

SUBMITTER: Liu Z

PROVIDER: S-EPMC2654228 | biostudies-literature | 2008 Sep

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of anti-beta-substituted gamma,delta-unsaturated amino acids: a highly selective asymmetric thio-Claisen rearrangement.

Liu Zhihua Z Qu Hongchang H Gu Xuyuan X Min Byoung J BJ Nichol Gary S GS Nyberg Joel J Hruby Victor J VJ

Organic letters 20080815 18

A novel synthesis of optically active anti-beta-substituted gamma,delta-unsaturated amino acids via a thio-Claisen rearrangement has been achieved. A 2,5-diphenylpyrrolidine was used as a C2-symmetric chiral auxiliary to control the stereochemistry, giving good yields and excellent diastereoselectivities and enantioselectivities. ...[more]

PMID: 18702500

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