%0 Journal Article
%T Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates
%A Julien Lefranc
%A Alberto Minassi
%A Jonathan Clayden
%J Beilstein Journal of Organic Chemistry
%D 2013
%I 
%R 10.3762/bjoc.9.70
%X N-Alkenyl ureas and N-alkenyl carbamates, like other N-acyl enamines, are typically nucleophilic at their ¦Â-carbon. However, by incorporating an ¦Á-aryl substituent, we show that they will also undergo attack at the ¦Â-carbon by organolithium nucleophiles, leading to the products of carbolithiation. The carbolithiation of E and Z N-alkenyl ureas is diastereospecific, and N-tert-butoxycarbonyl N-alkenyl carbamates give carbolithiation products that may be deprotected in situ to provide a new connective route to hindered amines.
%K carbamate
%K carbolithiation
%K carbometallation
%K organolithium
%K stereospecificity
%K styrene
%K urea
%U http://dx.doi.org/10.3762/bjoc.9.70