Enantioselective One-Pot Conjugate Addition of Grignard Reagents Followed by a Mannich Reaction

被引：18

作者：

Sebesta, Radovan ^{[1
]}

Bilcik, Filip ^{[1
]}

Fodran, Peter ^{[1
]}

机构：

[1] Comenius Univ, Fac Nat Sci, Dept Organ Chem, Bratislava 84215, Slovakia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 29期

关键词：

Asymmetric catalysis; Michael addition; Mannich reaction; Copper; Ferrocene; TANDEM; KETONES;

D O I：

10.1002/ejoc.201000773

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric addition of Grignard reagents to cyclohexenone, catalyzed by ferrocene diphosphanes, afforded chiral magnesium enolates. These enolates reacted in a one-pot arrangement with N-benzylidenetoluenesulfonamide to give beta-amino carbonyl compounds with three contiguous stereocenters. Two major diastereoisomers (dr = 60:40) of product with enantioselectivities up to 95 % ee were separated by flash chromatography.

引用

页码：5666 / 5671

页数：6

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