Remote chirality transfer in nucleophilic catalysis with N-(4-pyridinyl)-L-proline derivatives

被引：50

作者：

Kawabata, T ^{[1
]}

Stragies, R ^{[1
]}

Fukaya, T ^{[1
]}

Fuji, K ^{[1
]}

机构：

[1] Kyoto Univ, Inst Chem Res, Kyoto 6110011, Japan

来源：

CHIRALITY | 2003年 / 15卷 / 01期

关键词：

kinetic resolution; asymmetric induction; acylation; nucleophilic catalyst; amino acid;

D O I：

10.1002/chir.10166

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Chiral nucleophilic catalysts 5-15 were prepared starting from L-proline. Catalysts 9 and 14 promoted acylative kinetic resolution of racemic amino alcohol derivative 16 with selectivity factors of 8.1 and 11, respectively, at ambient temperature. Since chiral elements are not present in the catalytically active pyridine ring in these catalysts, chirality transfer from the remote stereogenic center to the reactive site (N-acylpyridinium) is suggested to be responsible for the differentiation between enantiomers. (C) 2002 Wiley-Liss, Inc.

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页码：71 / 76

页数：6

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