title: Enantioselective organo-SOMO cycloadditions: a catalytic approach to complex pyrrolidines from olefins and aldehydes.
abstract: 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 stereochemically complex pyrrolidine products with high chemical efficiency and enantiocontrol.
authors: Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA.
authors: Nathan T
authors: NT
authors: Jui
authors: Jeffrey A O
authors: JA
authors: Garber
authors: Fernanda Gadini
authors: FG
authors: Finelli
authors: David W C
authors: DW
authors: MacMillan
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D011759:Pyrrolidines