Cyclization Reactions through DDQ-Mediated Vinyl Oxazolidinone Oxidation

被引：74
|
作者：
Liu, Lei [1 ]
Floreancig, Paul E. [1 ]
机构：
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 14期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
C-H ACTIVATION; TRIISOPROPYLSILYL ENOL ETHERS; CARBON BOND FORMATION; CHIRAL ENAMIDES; ELECTROSTATIC STABILIZATION; OXOCARBENIUM IONS; LEWIS-ACID; AMIDES; REACTIVITY; FUNCTIONALIZATION;
D O I：
10.1021/ol901188q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Vinyl oxazolidinones react with DDQ to form alpha,beta-unsaturated acyliminium ions in a new method for forming electrophiles under oxidative conditions. Appended nucleophiles undergo 1,4-addition reactions with these intermediates to form cyclic vinyl oxazolidinones with good levels of diastereocontrol, highlighting a new approach to utilizing oxidative carbon-hydrogen bond functionalization to increase molecular complexity.
引用
收藏
页码：3152 / 3155
页数：4
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