Stereoselective Synthesis of 1,2,3,4-Tetrasubstituted Dienes from Allenoates and Aldehydes: An Observation of Phosphine-Induced Chemoselectivity

被引：44

作者：

Xu, Silong

Zou, Wen

Wu, Guiping

Song, Haibin

He, Zhengjie ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 15期

基金：

中国国家自然科学基金;

关键词：

CATALYZED 3+2 CYCLOADDITION; HIGHLY FUNCTIONALIZED TETRAHYDROPYRIDINES; WITTIG OLEFINATION; ENYNE METATHESIS; TRISUBSTITUTED 1,3-DIENES; MEDIATED OLEFINATION; EFFICIENT SYNTHESIS; 4+2 ANNULATION; ALLENES; SELECTIVITY;

D O I：

10.1021/ol101429z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phosphine-mediated olefination between a-substituted allenoates and aldehydes to form 1,2,3,4-tetrasubstituted 1,3-dienes is presented. High levels of chemo- and diastereoselectivity and yield are obtained for a wide scope of substrates with the choice of appropriate phosphines. This reaction evidences the capacity of phosphines in the control of reaction pathways and provides a highly efficient synthetic method for tetrasubstituted conjugated dienes.

引用

页码：3556 / 3559

页数：4

共 60 条

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