有机催化硫亲核试剂对氮丙啶的动力学拆分。

An Organocatalytic Kinetic Resolution of Aziridines by Thiol Nucleophiles.

机构信息

Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.

Department of Chemistry, the Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.

出版信息

Org Lett. 2021 Jan 15;23(2):554-558. doi: 10.1021/acs.orglett.0c04074. Epub 2020 Dec 31.

DOI:10.1021/acs.orglett.0c04074

PMID:33382271

Abstract

We report the first organocatalytic kinetic resolution of unactivated aziridines by sulfur nucleophiles with excellent enantioselectivity. A suitable chiral phosphoric acid was found to catalyze the intermolecular ring opening under mild conditions, furnishing a range of highly enantioenriched β-amino thioethers and aziridines, both of which are useful synthetic building blocks.

摘要

我们报道了首例通过硫亲核试剂对未活化的氮丙啶进行的有机催化动力学拆分，具有优异的对映选择性。研究发现，合适的手性磷酸可以在温和条件下催化分子间的开环反应，生成一系列高对映体富集的β-氨基硫醚和氮丙啶，它们都是有用的合成砌块。