Hindered ureas as masked isocyanates: Facile carbamoylation of nucleophiles under neutral conditions

…, GC Lloyd??Jones, KI Booker??Milburn

Index: Hutchby, Marc; Houlden, Chris E.; Gair Ford; Tyler, Simon N. G.; Gagne, Michel R.; Lloyd-Jones, Guy C.; Booker-Milburn, Kevin I. Angewandte Chemie - International Edition, 2009 , vol. 48, # 46 p. 8721 - 8724

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Citation Number: 44

Abstract

Ureas are normally rather inert towards alcohols, amines, and thiols: they require high temperatures, acidic or basic conditions, or metal catalysis, to undergo nucleophilic substitution reactions.[1] Whilst this feature makes them robust protecting groups for aromatic and aliphatic amines, it somewhat limits their subsequent utility. Herein we demonstrate that, in stark contrast to this general behavior, hindered trisubstituted ureas ...