Enantioselective formal [2+2] cycloaddition of ketenes with nitroso compounds catalyzed by N-heterocyclic carbenes

被引：51

作者：

Wang, Tong ^{[1
]}

Huang, Xue-Liang ^{[1
]}

Ye, Song ^{[1
]}

机构：

[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 21期

基金：

美国国家科学基金会;

关键词：

HYDROXYCARBOXYLIC ACID-DERIVATIVES; ALPHA-KETOESTERS; BENZOIN CONDENSATION; ASYMMETRIC-SYNTHESIS; ALLYLIC ALKYLATION; ORGANOCATALYSIS; OXIDATION; KETONES;

D O I：

10.1039/c0ob00249f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral N-heterocyclic carbenes were found to be efficient catalysts for the formal [2+2] cycloaddition reaction of alkyl(aryl)ketenes and nitroso compounds to give the corresponding 1,2-oxazetidin-3-ones in moderate to good yields with high enantioselectivities. Reductive ring-opening of the oxazetidinones give the corresponding alpha-hydroxy acid derivatives in good yields.

引用

页码：5007 / 5011

页数：5

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