α-酰胺基酮与乙烯基锍盐反应的环氧环化反应。试剂与底物控制及动力学拆分

Epoxy-annulations by reactions of alpha-amido ketones with vinyl sulfonium salts. Reagent versus substrate control and kinetic resolution.

作者信息

Unthank Matthew G, Tavassoli Bahareh, Aggarwal Varinder K

机构信息

School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS United Kingdom.

出版信息

Org Lett. 2008 Apr 3;10(7):1501-4. doi: 10.1021/ol800318h. Epub 2008 Mar 13.

DOI:10.1021/ol800318h

PMID:18336037

Abstract

Diphenyl vinyl sulfonium salt and chiral amido-ketones undergo highly diastereoselective epoxy-annulation reactions in good yield. The use of a chiral vinyl sulfonium salt dominates the stereochemical outcome of the annulation reaction (reagent control is greater than substrate control), and this has allowed the kinetic resolution of racemic amido-ketones to be achieved.

摘要

二苯基乙烯基锍盐与手性酰胺酮能以良好的产率进行高度非对映选择性的环氧化反应。使用手性乙烯基锍盐主导了环化反应的立体化学结果（试剂控制大于底物控制），这使得外消旋酰胺酮的动力学拆分得以实现。