Highly active polymer-supported (salen)Al catalysts for the enantioselective addition of cyanide to α,β-unsaturated imides

被引:58
|
作者
Madhavan, Nandita [1 ]
Weck, Marcus [1 ,2 ,3 ]
机构
[1] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA
[2] NYU, Dept Chem, New York, NY 10003 USA
[3] NYU, Inst Mol Design, New York, NY 10003 USA
关键词
aluminum; asymmetric catalysis; conjugated addition; salen; supported catalysis;
D O I
10.1002/adsc.200700491
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this contribution, we describe polymer-supported (R,R)-(salen)AlCl complexes that were immobilized on poly(norbornene)s and display excellent activities and enantioselectivies as catalysts for the 1,4-conjugate addition of cyanide to alpha,beta-unsaturated imides. These supported catalysts could be recycled up to 5 times without compromising catalyst activities or selectivities. Furthermore, the catalyst loadings could be reduced from 10-15 mol%, the common catalyst loadings for non-supported (salen)Al catalysts, to 5 mol%, a decrease of metal content by 50-66%, without lowering product yields or enantioselectivities. Kinetic studies indicated that the polymer-supported catalysts are significantly more active than their corresponding unsupported analogues, which makes this catalyst system key to a successful implementation of this catalytic transformation into the fine chemical and pharmaceutical industries.
引用
收藏
页码:419 / 425
页数:7
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