Phosphine-boronates: efficient bifunctional organocatalysts for Michael addition

被引：52

作者：

Basle, Olivier ^{[1
,2
]}

Porcel, Susana ^{[1
,2
]}

Ladeira, Sonia ^{[3
]}

Bouhadir, Ghenwa ^{[1
,2
]}

Bourissou, Didier ^{[1
,2
]}

机构：

[1] Univ Toulouse, UPS, LHFA, F-31062 Toulouse, France

[2] CNRS, LHFA, UMR 5069, F-31062 Toulouse, France

[3] Univ Toulouse 3, Inst Chim Toulouse FR 2599, F-31062 Toulouse 9, France

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 37期

关键词：

FRUSTRATED LEWIS PAIRS; ASYMMETRIC CATALYSIS; CONJUGATE ADDITIONS; HYDROGENATION; IMINES;

D O I：

10.1039/c2cc30399j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Phosphine-boronates R2P(o-C6H4)B(OR ')(2) have been evaluated as bifunctional organocatalysts for the Michael addition of malonate pronucleophiles to methylvinylketone. The presence of the Lewis acidic boron center adjacent to phosphorus significantly improves catalytic performance. Isolation and complete characterization of a key intermediate, namely a beta-phosphonium enolate, substantiate the role of the Lewis acidic moiety in the catalytic process.

引用

页码：4495 / 4497

页数：3

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