N-heterocyclic carbene-catalyzed conjugate additions of alcohols

EM Phillips, M Riedrich, KA Scheidt

Index: Phillips, Eric M.; Riedrich, Matthias; Scheidt, Karl A. Journal of the American Chemical Society, 2010 , vol. 132, # 38 p. 13179 - 13181

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Citation Number: 112

Abstract

An efficient intermolecular conjugate addition of alcohols to activated alkenes catalyzed by N-heterocyclic carbenes has been developed. With 5 mol% of the free carbene derived from IMes· HCl, unsaturated ketones and esters are competent substrates, and a variety of primary and secondary alcohols can be employed as the nucleophile. No oligomerization is observed under these mild conditions for effective hydroalkoxylation. In addition to ...