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由易于组装的手性4-N,N-二烷基氨基吡啶衍生物促进的不对称酰基转移反应。

Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivatives.

作者信息

Dálaigh Ciarán O, Hynes Stephen J, O'Brien John E, McCabe Thomas, Maher Declan J, Watson Graeme W, Connon Stephen J

机构信息

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

出版信息

Org Biomol Chem. 2006 Jul 21;4(14):2785-93. doi: 10.1039/b604632k. Epub 2006 Jun 20.

Abstract

The development of a new class of chiral 4-N,N-dialkylaminopyridine acyl-transfer catalysts capable of exploiting both van der Waals (pi) and H-bonding interactions to allow remote chiral information to stereochemically control the kinetic resolution of sec-alcohols with moderate to excellent selectivity (s = 6-30). Catalysts derived from (S)-alpha,alpha-diarylprolinol are considerably superior to analogues devoid of a tertiary hydroxyl moiety and possess high activity and selectivity across a broad range of substrates.

摘要

一类新型手性4-N,N-二烷基氨基吡啶酰基转移催化剂的开发,这类催化剂能够利用范德华(π)和氢键相互作用,使远程手性信息通过立体化学控制仲醇的动力学拆分,具有中等至优异的选择性(s = 6-30)。源自(S)-α,α-二芳基脯氨醇的催化剂明显优于不含叔羟基部分的类似物,并且在广泛的底物范围内具有高活性和选择性。

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