Dataset Information
Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates.
Ontology highlight
ABSTRACT:
SUBMITTER: Lefranc J
PROVIDER: S-EPMC3628850 | biostudies-literature | 2013
REPOSITORIES: biostudies-literature
Publications
Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates.
Beilstein journal of organic chemistry 20130328
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 connec ...[more]