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β-羟基磺胺亚胺在催化不对称苯基转移反应中用于合成二芳基甲醇的应用。

Application of beta-hydroxysulfoximines in catalytic asymmetric phenyl transfer reactions for the synthesis of diarylmethanols.

作者信息

Sedelmeier Jörg, Bolm Carsten

机构信息

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056, Aachen, Germany.

出版信息

J Org Chem. 2007 Nov 9;72(23):8859-62. doi: 10.1021/jo7016718. Epub 2007 Oct 11.

Abstract

Enantiomerically enriched diarylmethanols have been prepared by catalyzed asymmetric phenyl transfer reactions onto aromatic aldehydes with use of readily available beta-hydroxysulfoximines as catalysts. As the aryl source, combinations of diethylzinc with either diphenylzinc or triphenylborane have been applied affording arylphenylmethanols with up to 93% ee in good yields. Various functionalized aldehydes and heterocyclic substrates are tolerated, yielding synthetically relevant products.

摘要

通过使用易于获得的β-羟基磺胺作为催化剂,将催化不对称苯基转移反应应用于芳香醛上,制备了对映体富集的二芳基甲醇。作为芳基源,已应用二乙基锌与二苯基锌或三苯基硼烷的组合,以良好的产率提供对映体过量高达93%的芳基苯基甲醇。各种官能化醛和杂环底物都能耐受,从而得到具有合成相关性的产物。

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