One-Pot Three-Component Catalytic Enantioselective Synthesis of Homoallylboronates

被引：80

作者：

Ibrahem, Ismail ^{[1
]}

Breistein, Palle ^{[1
]}

Cordova, Armando ^{[1
,2
,3
]}

机构：

[1] Mid Sweden Univ, Dept Nat Sci Engn & Math, SE-85170 Sundsvall, Sweden

[2] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, Stockholm, Sweden

[3] Stockholm Univ, Berzelii Ctr EXSELENT, Stockholm, Sweden

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 50期

关键词：

asymmetric catalysis; boron; conjugate additions; multicomponent reactions; Wittig reactions; ASYMMETRIC ALLYLIC ALKYLATION; BORON CONJUGATE ADDITIONS; TRANSITION-METAL; MULTICOMPONENT REACTIONS; 1,6-CONJUGATE ADDITION; CASCADE CATALYSIS; BETA-BORATION; ALDEHYDES; HYDROBORATION; ESTERS;

D O I：

10.1002/anie.201105458

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

No longer a simple bor(ation): The title reaction between bis(pinacolato)diboron, enals, and 2-(triphenylphosphoranylidene)acetates employing bench-stable copper salts and a simple chiral amine co-catalyst is presented (see scheme). The reaction proceeds through a catalytic asymmetric conjugate borane addition/Wittig sequence wherein the β-boration step is 1,4-selective and gives the corresponding homoallylboronate products with high enantiomeric ratios. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12036 / 12041

页数：6

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