Organic Letters 2011-02-18

Internal Lewis acid assisted hydrogen bond donor catalysis.

Sonia S So, Julie A Burkett, Anita E Mattson

Index: Org. Lett. 13(4) , 716-9, (2011)

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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.