title: Asymmetric construction of spirocyclopentenebenzofuranone core structures via highly selective phosphine-catalyzed [3 + 2] cycloaddition reactions.
abstract: An efficient organocatalytic asymmetric [3 + 2] cycloaddition reaction between 3-substituted methylenebenzofuranone derivatives and diverse Morita-Baylis-Hillman carbonates to provide complex polysubstituted spirocyclopentenebenzofuranone scaffolds in a single step is reported. C2-symmetric phospholanes were efficient nucleophilic catalysts of this transformation under mild conditions, providing reaction products comprised of three consecutive stereocenters, including one all-carbon center, with excellent enantioselectivity.
authors.affiliation: The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Cell and Molecular Biology, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Klaus
authors.initials: K
authors.lastname: Albertshofer
authors.forename: Bin
authors.initials: B
authors.lastname: Tan
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D001572:Benzofurans / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D010720:Phosphines; C044646:phosphine