有机催化的三取代丙烯腈的立体选择性环氧化反应。

Organocatalytic stereoselective epoxidation of trisubstituted acrylonitriles.

机构信息

Dipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, 84084, Fisciano, Italy.

出版信息

J Org Chem. 2011 Jan 21;76(2):676-9. doi: 10.1021/jo102020a. Epub 2010 Dec 22.

DOI:10.1021/jo102020a

Abstract

The first diastereospecific and enantioselective epoxidation of trans-2-aroyl-3-arylacrylonitriles by means of the commercially available diaryl L-prolinol/tert-butyl hydroperoxide system has been developed. These diversely functionalized epoxides were obtained in excellent yield (up to 99%), complete diastereoselectivity for the trans-isomer, and good enantioselectivity (up to 84% ee). Highly enantioenriched epoxides can be easily obtained after a single crystallization (ee > 90%).

摘要

通过商业可得的二芳基 L-脯氨醇/叔丁基过氧化氢体系，首次对反式-2-芳基-3-芳基丙烯腈进行了非对映选择性和对映选择性环氧化反应。这些官能化的环氧化物以优异的收率（高达 99%）、对反式异构体的完全非对映选择性和良好的对映选择性（高达 84%ee）得到。经过一次结晶后，可以很容易地得到高对映体过量的环氧化物（ee>90%）。

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