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
收藏
页码：12036 / 12041
页数：6
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