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  • Title: Stereogenic phosphorus-induced diastereoselective formation of chiral carbon during nucleophilic addition of chiral H-P species to aldehydes or ketones.
    Author: Zhang H, Sun YM, Yao L, Ji SY, Zhao CQ, Han LB.
    Journal: Chem Asian J; 2014 May; 9(5):1329-33. PubMed ID: 24591454.
    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.
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