Stereoselective preparation of (E)- and (Z)-di- and trisubstituted 1,3-butadienes

被引：4

作者：

Takeda, Takeshi ^{[1
]}

Tateishi, Keiichiro ^{[1
]}

Tsubouchi, Akira ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, Koganei, Tokyo 1848588, Japan

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 26期

关键词：

Conjugated dienes; Stereoselective synthesis; Allyltitanocenes; Ketones; Peterson elimination; HIGHLY DIASTEREOSELECTIVE ADDITION; CATALYZED 4+2 CYCLOADDITION; ETHYL CYCLOPROPYLIDENEACETATE; CROSS-METATHESIS; INTERNAL ALKYNES; FORMAL SYNTHESIS; DIENES; 1,3-DIENES; ALLYLTITANOCENES; OLEFINATION;

D O I：

10.1016/j.tetlet.2015.04.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of gamma-(trimethylsilyl)allyltitanocenes, generated by the desulfurizative titanation of trimethylsilyl-substituted allylic sulfides with the titanocene(II)-1-butene complex, with ketones produced beta-hydroxy silanes with good to complete anti-selectivity. Both (E)- and (Z)-1,1-disubstituted as well as 1,1,2-trisubstituted 1,3-butadienes are obtained stereoselectively by their Peterson elimination under acidic or basic conditions. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：4016 / 4021

页数：6

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