Axially Chiral Phosphine-Oxazoline Ligands in Silver(I)-Catalyzed Asymmetric Mannich Reaction of Aldimines with Trimethylsiloxyfuran

被引：47

作者：

Deng, Hong-Ping ^{[1
]}

Wei, Yin ^{[1
]}

Shi, Min ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 17期

基金：

中国国家自然科学基金;

关键词：

aldimines; asymmetric Mannich reaction; axially chiral phosphine-oxazoline ligands; silver acetate; trimethylsiloxyfuran; ENANTIOSELECTIVE VINYLOGOUS MANNICH; ACID; BUTENOLIDES; ADDITIONS;

D O I：

10.1002/adsc.200900550

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new asymmetric catalytic system for the Mannich reaction of aldimines with trimethylsiloxyfuran is described. The combination of an axially chiral phosphine-oxazoline ligand (S)-2-[(R)-2'-(diphenylphosphino)-1,1'-binaphthyl-2-yl]-4-phenyl-4,5-dihydrooxazole with silver acetate and 2,2,2-trifluoroacetic acid is a very effective catalytic system in the asymmetric Mannich reaction of various aldimines with trimethylsiloxyfuran in dichloromethane at -78 degrees C, affording the corresponding adducts in up to 99% yield, 99:1 (dr) and 99% ee (major diastereoisomer) under mild conditions.

引用

页码：2897 / 2902

页数：6

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