Iron-Catalyzed Unexpected Easy Access to Stereodefined Trimethylsilyl Vinyl Ketenes

被引：12

作者：

Chai, Guobi ^{[1
]}

Fu, Chunling ^{[1
]}

Ma, Shengming ^{[1
]}

机构：

[1] Zhejiang Univ, Lab Mol Recognit & Synth, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 16期

关键词：

STEREOSELECTIVE CONJUGATE ADDITION; HIGHLY SUBSTITUTED CYCLOPENTENONES; FISCHER CARBENE COMPLEXES; HETEROAROMATIC-COMPOUNDS; ANNULATION APPROACH; 4+2 CYCLOADDITIONS; GRIGNARD-REAGENTS; (TRIALKYLSILYL)VINYLKETENES; VINYLKETENES; GENERATION;

D O I：

10.1021/ol3016176

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereodefined trimethylsilyl vinyl ketenes with polysubstitution have been synthesized highly regio- and stereoselectively via an iron-catalyzed reaction of 2-trimethylsilyl-2,3-allenoates with Grignard reagents in good to excellent yields. The reaction was believed to proceed via a conjugate addition and elimination mechanism. Applications of the products for the synthesis of stereodefined alpha-silyl-beta,gamma-unsaturated enones, a stereodefined triene, and polysubstituted phenols have been carefully demonstrated.

引用

页码：4058 / 4061

页数：4

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