title: Diastereoselective B(C6F5)3-Catalyzed Reductive Carbocyclization of Unsaturated Carbohydrates.
abstract: A B(C6F5)3-catalyzed method for the selective conversion of unsaturated carbohydrates to cyclopentanes and cyclopropanes is disclosed. Catalyst activation of tertiary silanes generates the ion pair [(C6F5)3B-H][ROSi2] whose components synergistically activate C-O bonds for diastereoselective C-C bond formation. Sila-THF cations are invoked as key intermediates facilitating carbocyclizations. Complex chiral synthons are thereby obtained in a single pot.
authors: Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.
authors: Trandon A
authors: TA
authors: Bender
authors: Department of Chemistry, Elon University , Elon, North Carolina 27244, United States.
authors: Jennifer A
authors: JA
authors: Dabrowski
authors: Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.
authors: Hongyu
authors: H
authors: Zhong
authors: Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.
authors: Michel R
authors: MR
authors: Gagné
mesh_terms: D001880:Boranes / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D005466:Fluorocarbons
chemical_list: D001880:Boranes; D002241:Carbohydrates; D003517:Cyclopentanes; D003521:Cyclopropanes; D006845:Hydrocarbons, Fluorinated; C547049:tris(pentafluorophenyl)borane; D005466:Fluorocarbons