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芳基化、去氧奎宁生物碱催化的噁唑烷酮与硫醇亲核试剂的动态动力学拆分。

The dynamic kinetic resolution of azlactones with thiol nucleophiles catalyzed by arylated, deoxygenated cinchona alkaloids.

机构信息

School of Chemistry, Centre for Synthesis and Chemical Biology, Trinity Biomedical Sciences Institute, University of Dublin, Trinity College, Dublin 2, Ireland.

出版信息

J Org Chem. 2012 Mar 2;77(5):2407-14. doi: 10.1021/jo202662d. Epub 2012 Feb 22.

Abstract

A significant improvement of the available organocatalytic methods (in terms of product substrate scope and product enantiomeric excess) for the generation of enantioenriched α-amino acid thioesters via the dynamic kinetic resolution of azlactones is reported. C-9 arylated cinchona alkaloid catalysts have been found to be considerably superior to other bifunctional alkaloid catalysts as the promoters of this asymmetric process.

摘要

报告了一种通过动态动力学拆分氮杂环丁酮来生成对映体富集的α-氨基酸硫代酯的有机催化方法的显著改进(在产物底物范围和产物对映体过量方面)。已经发现 C-9 芳基化金鸡纳生物碱催化剂作为该不对称过程的促进剂,比其他双功能生物碱催化剂优越得多。

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