Nucleophilic phosphine organocatalysis

被引：947

作者：

Methot, JL ^{[1
]}

Roush, WR ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 9-10期

关键词：

catalysis; cycloaddition; Morita-Baylis-Hillman; phosphine; resolution; umpolung;

D O I：

10.1002/adsc.200404087

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Phosphines have recently become popular choices as nucleophilic catalysts in organic synthesis. The unique reactivity of phosphines compared to amines has allowed the discovery of new nucleophilic addition reactions at the alpha- and gamma-positions of unsaturated carbonyl compounds, as well as novel [3 + 2] and [4 + 2] cycloaddition reactions of activated alkynes and alkenes. The accessibility of chiral phosphines has rendered several of these transformations enantioselective and has made possible the kinetic resolution of racemic secondary alcohols by phosphine-catalyzed acylation. This mini-review presents recent advances in nucleophilic phosphine organocatalysis for carbon-carbon bond formation.

引用

页码：1035 / 1050

页数：16

共 113 条

[1] Carboxylates as pronucleophiles in the phosphine-catalyzed γ-addition reaction [J].