title: Organocatalytic enantioselective synthesis of both diastereomers of alpha-hydroxyphosphinates.
abstract: Racemic alpha-acylphosphinates and formylphosphinate hydrate were used directly as the substrates in a proline derivative-catalyzed cross aldol reaction with ketones. Because of the preexisting phosphorus stereogenic center, a mixture of two diastereomers of the corresponding alpha-hydroxyphosphinates was obtained in this reaction. Good to high enantioselectivities (up to 99% ee) were obtained simultaneously for the two diastereomers in good yields. Good diastereoselectivities were also obtained when the reaction generates an additional carbon stereogenic center.
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA.
authors.forename: Sampak
authors.initials: S
authors.lastname: Samanta
authors.forename: Sandun
authors.initials: S
authors.lastname: Perera
authors.forename: Cong-Gui
authors.initials: CG
authors.lastname: Zhao
mesh_terms: D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010721:Phosphinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D010721:Phosphinic Acids