title: Dual amine and palladium catalysis in diastereo- and enantioselective allene carbocyclization reactions.
abstract: A pyrrolidine and Pd catalyzed diastereoselective carbocyclization of aldehyde and ketone-linked allenes has been developed. The cooperative organo/metal-catalyzed cyclization reaction, which presumably proceeds via an enamine intermediate, is efficient and broad in scope. Also, it has been extended to a catalytic asymmetric variant using diarylprolinol-based organocatalysts to afford substituted cyclopentane and pyrrolidine reaction products in up to 82% ee.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.
authors.forename: Meiling
authors.initials: M
authors.lastname: Li
authors.forename: Swarup
authors.initials: S
authors.lastname: Datta
authors.forename: David M
authors.initials: DM
authors.lastname: Barber
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines; D003517:Cyclopentanes; D007659:Ketones; D010165:Palladium