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  • Title: Enantioselective synthesis of the optically active alpha-methylene-beta-hydroxy esters, equivalent compounds to Morita-Baylis-Hillman adducts, using successive asymmetric aldol reaction and oxidative deselenization.
    Author: Shiina I, Yamai YS, Shimazaki T.
    Journal: J Org Chem; 2005 Sep 30; 70(20):8103-6. PubMed ID: 16277334.
    Abstract:
    [Chemical reaction: See text] The asymmetric aldol reaction of a tetra-substituted ketene silyl acetal including an alkylseleno group with aldehydes has been developed by the promotion of Sn(OTf)2 coordinated with a chiral diamine to afford the corresponding aldols having chiral quaternary centers at the alpha-positions. The facile oxidative deselenization of these aldol compounds produces optically active alpha-methylene-beta-hydroxy esters which correspond to adducts prepared by the asymmetric Morita-Baylis-Hillman reaction.
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