A New Family of Cinchona-Derived Amino Phosphine Precatalysts: Application to the Highly Enantio- and Diastereoselective Silver-Catalyzed Isocyanoacetate Aldol Reaction

被引：206

作者：

Sladojevich, Filippo ^{[1
]}

Trabocchi, Andrea ^{[2
]}

Guarna, Antonio ^{[2
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Univ Florence, Dipartimento Chim U Schiff, I-50019 Sesto Fiorentino, Italy

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 06期

基金：

英国工程与自然科学研究理事会;

关键词：

CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEXES; BIFUNCTIONAL ASYMMETRIC CATALYSIS; ALPHA-ISOCYANOCARBOXYLATES; FERROCENYLAMINE LIGANDS; PINCER COMPLEXES; MICHAEL ADDITION; ALDEHYDES; ACIDS; OXAZOLINES;

D O I：

10.1021/ja110534g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Anew class of readily accessible chiral amino-phosphine precatalysts derived from 9-amino(9-deoxy) epicinchona alkaloids has been developed. In combination with Ag(I) salts, these amino-phosphines performed as effective cooperative Bronsted base/Lewis acid catalysts in the asymmetric aldol reaction of isocyanoacetate nucleophiles. Under optimal conditions, high diastereoselectivities (up to 98%) and enantioselectivities (up to 98%) were obtained.

引用

页码：1710 / 1713

页数：4

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