Asymmetric Epoxidation Catalyzed by α,α-Dimethylmorpholinone Ketone. Methyl Group Effect on Spiro and Planar Transition States

被引：18

作者：

Wong, O. Andrea ^{[1
]}

Wang, Bin ^{[1
]}

Zhao, Mei-Xin ^{[1
]}

Shi, Yian ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 16期

基金：

美国国家卫生研究院;

关键词：

OXAZOLIDINONE-CONTAINING KETONES; CHIRAL DIOXIRANE; ENANTIOSELECTIVE EPOXIDATION; TERMINAL OLEFINS; HYDROGEN-PEROXIDE; PRIMARY OXIDANT; CIS-OLEFINS; CYCLOPENTANONES; REARRANGEMENT; OXIDATION;

D O I：

10.1021/jo900739q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric epoxidation of olefins by using an alpha,alpha-dimethylmorpholinone-containing chiral ketone catalyst (4) has been investigated. This ketone, which has the combined features of several previously studied catalysts, is an effective catalyst for trans- and trisubstituted olefins, and up to 97% ee has been achieved. The alpha,alpha-dimethyl group has significant impact oil spiro and planar transition states.

引用

页码：6335 / 6338

页数：4

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