Internal Lewis acid assisted hydrogen bond donor catalysis.

Organic letters (2011-01-14)
Sonia S So, Julie A Burkett, Anita E Mattson
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Schreiner′s Catalyst
Sigma-Aldrich
Potassium 3-ethoxycarbonylbenzoyltrifluoroborate
Sigma-Aldrich
Mattson Boronate Urea Pinacol Ester

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