A versatile catalyst for asymmetric reactions of carbonyl groups working purely by activation through hydrogen bonding: Mukaiyama-aldol, hetero Diels-Alder and Friedel-Crafts reactions

被引：105

作者：

Zhuang, W

Poulsen, TB

Jorgensen, KA ^{[1
]}

机构：

[1] Aarhus Univ, Danish Natl Res Fdn, DK-8000 Aarhus, Denmark

[2] Aarhus Univ, Ctr Catalysis, Dept Chem, DK-8000 Aarhus, Denmark

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 18期

关键词：

D O I：

10.1039/b507778h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bis-sulfonamides are demonstrated to be promising candidates for the efficient activation of carbonyl compounds through hydrogen bonding. Exemplified by three carbonyl addition reactions: Mukaiyama-aldol, hetero Diels-Alder and Friedel-Crafts reactions we show that bis-triamides or bis-nonaflamides of commercially available chiral diamines act as chiral Br phi nsted-acid catalysts, leading to the optically active products in moderate to excellent yields and with enantioselectivities up to 73% ee.

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页码：3284 / 3289

页数：6

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