A Facile, One-Pot Synthesis of β-Substituted (Z)-Acrylonitriles Utilizing an α-Diaminoboryl Carbanion

被引：33

作者：

Tomioka, Takashi ^{[1
]}

Takahashi, Yusuke ^{[1
]}

Vaughan, Trey G. ^{[1
]}

Yanase, Takayoshi ^{[1
]}

机构：

[1] Univ Mississippi, Dept Chem & Biochem, University, MS 38677 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 10期

关键词：

HINDERED ORGANOBORON GROUPS; DIMESITYLBORON STABILIZED CARBANIONS; BAYLIS-HILLMAN REACTION; ORGANIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; WITTIG REACTION; ALPHA; BETA-UNSATURATED CYANIDES; ALIPHATIC-ALDEHYDES; SELECTIVE SYNTHESIS; CARBONYL-COMPOUNDS;

D O I：

10.1021/ol100534s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple three-step single-pot procedure for Z-stereoselective synthesis of beta-monosubstituted acrylonitriles has been established. The reaction involves olefination of aldehydes with an in situ generated alpha-diaminoboryl carbanion species. Various aromatic and aliphatic aldehydes were smoothly converted into the corresponding (Z)-olefin products (up to 96:4 ratio) in good yields (80-98%).

引用

页码：2171 / 2173

页数：3

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