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
收藏
页码：5007 / 5011
页数：5
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