title: Stereogenic phosphorus-induced diastereoselective formation of chiral carbon during nucleophilic addition of chiral H-P species to aldehydes or ketones.
abstract: P,C-stereogenic α-hydroxyl phosphinates or phosphine oxides were prepared from the additions of (RP)-phosphinate to ketones or (RP)-phosphine oxide to aldehydes, respectively, catalyzed by bases at room temperature in up to >99:1 diasteromeric ratio (d.r.P/d.r.C) and 99 % yields. The diastereoselectivity was induced by reversible equilibrium and different stabilities between two diastereomers of adduct, which was caused by the spatial interaction between menthoxyl or menthyl to alkyl groups of aldehydes or ketones.
authors.affiliation: College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, Shandong 252059 (China), Fax: (+86) 6359239121.
authors.forename: He
authors.initials: H
authors.lastname: Zhang
authors.forename: Yong-Ming
authors.initials: YM
authors.lastname: Sun
authors.forename: Lan
authors.initials: L
authors.lastname: Yao
authors.forename: Si-Yu
authors.initials: SY
authors.lastname: Ji
authors.forename: Chang-Qiu
authors.initials: CQ
authors.lastname: Zhao
authors.forename: Li-Biao
authors.initials: LB
authors.lastname: Han
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D007659:Ketones; D009943:Organophosphorus Compounds; D010720:Phosphines
keywords: aldehydes; asymmetric synthesis; diastereoselectivity; ketones; phosphorus