Catalytic Carbon Insertion into the β-Vinyl C-H Bond of Cyclic Enones with Alkyl Diazoacetates

被引：29

作者：

Lee, Sung Il ^{[1
,2
]}

Kang, Byung Chul ^{[1
]}

Hwang, Geum-Sook ^{[2
]}

Ryu, Do Hyun ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

[2] Korea Basic Sci Inst, Seoul 136713, South Korea

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 07期

关键词：

ALPHA-SUBSTITUTED ACROLEINS; ASYMMETRIC ROSKAMP REACTION; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; DIAZOESTERS; KETONES; CONSTRUCTION; CYCLOPROPANATION; CONVERSION; PRECURSOR;

D O I：

10.1021/ol4000026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of the boron Lewis acid catalyzed C-SP2-H functionalization of cyclic enones was achieved using diazoacetates. The insertion of the carbon atom of diazoacetates utilizes BF3 center dot Et2O or a newly designed oxazaborolidinium ion as a catalyst to afford beta-functionalized cyclic enones from simple cyclic enones In a single step and high yields. The reaction mechanism was investigated with deuterium labeled 2-cyclohexen-1-one.

引用

页码：1428 / 1431

页数：4

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