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  • Title: Asymmetric synthesis of β-hydroxy-α-amino phosphonic acid derivatives via organocatalytic direct aldol reaction of α-isothiocyanato phosphonates with aldehydes.
    Author: Han WY, Zhao JQ, Wu ZJ, Zhang XM, Yuan WC.
    Journal: J Org Chem; 2013 Oct 18; 78(20):10541-7. PubMed ID: 24053407.
    Abstract:
    α-Isothiocyanato phosphonates are first used as nucleophiles to react with aldehydes for the asymmetric synthesis of β-hydroxy-α-amino phosphonic acid derivatives. The process is catalyzed by a quinine-derived thiourea via cascade aldol/cyclization reaction, affording a wide range of protected β-hydroxy-α-amino phosphonates containing adjacent quaternary-tertiary stereocenters in up to 93% yield, up to 81% ee, and >99:1 dr. This work represents the first example of α-isothiocyanato phosphonates serving as nucleophiles that are used in the catalytic asymmetric synthesis.
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