Ontology highlight
ABSTRACT:
SUBMITTER: Jui NT
PROVIDER: S-EPMC3408613 | biostudies-literature | 2012 Jul
REPOSITORIES: biostudies-literature
Journal of the American Chemical Society 20120710 28
A new method to rapidly generate pyrrolidines via a SOMO-activated enantioselective (3 + 2) coupling of aldehydes and conjugated olefins has been accomplished. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnish a cationic intermediate which is vulnerable to nucleophilic addition of a tethered amine group. A range of olefins, including styrenes and dienes, are shown to provide stereochemicall ...[more]