Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates
Open Access
- 28 March 2013
- journal article
- Published by Beilstein Institut in Beilstein Journal of Organic Chemistry
- Vol. 9 (1) , 628-632
Abstract
N-Alkenyl ureas and N-alkenyl carbamates, like other N-acyl enamines, are typically nucleophilic at their β-carbon. However, by incorporating an α-aryl substituent, we show that they will also undergo attack at the β-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.Keywords
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