title: Asymmetric synthesis of methylenetetrahydrofurans by palladium-catalyzed [3 + 2] cycloaddition of trimethylenemethane with aldehydes--a novel ligand design.
abstract: The palladium-catalyzed [3 + 2] cycloaddition of trimethylenemethane (TMM) with aldehydes is a direct and efficient route to methylenetetrahydrofurans. Herein we describe the first asymmetric synthesis of methylenetetrahydrofurans utilizing a palladium-TMM complex in the presence of a novel phosphoramidite ligand possessing a stereogenic phosphorus. The method allows for the formation of chiral disubstituted tetrahydrofurans in good yields and enantioselectivities.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Dustin A
authors.initials: DA
authors.lastname: Bringley
authors.forename: Steven M
authors.initials: SM
authors.lastname: Silverman
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D008024:Ligands; C522820:trimethylenemethane; D010165:Palladium; D008697:Methane