Internal Lewis Acid Assisted Hydrogen Bond Donor Catalysis

被引：61

作者：

So, Sonia S. ^{[1
]}

Burkett, Julie A. ^{[1
]}

Mattson, Anita E. ^{[1
]}

机构：

[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 04期

关键词：

FRIEDEL-CRAFTS ALKYLATION; ASYMMETRIC CATALYSIS; INDOLES; NITROALKENES; THIOUREA; UREA; ORGANOCATALYST; COORDINATION; RECOGNITION; RECEPTORS;

D O I：

10.1021/ol102899y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Boronate ureas are introduced as a new class of noncovalent catalysts for conjugate addition reactions with enhanced activity. Through intramolecular coordination of the urea functionality to a strategically placed Lewis acid, rate enhancements up to 10 times that of more conventional urea catalysts are observed. The tunable nature of boronate ureas is a particularly attractive feature and enables the rational design of catalysts for optimal performance, in terms of both activity and stereocontrol, in new bond-forming processes.

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页码：716 / 719

页数：4

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