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  • Title: A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: applications in asymmetric synthesis.
    Author: Sarabia F, Vivar-García C, García-Castro M, García-Ruiz C, Martín-Gálvez F, Sánchez-Ruiz A, Chammaa S.
    Journal: Chemistry; 2012 Nov 19; 18(47):15190-201. PubMed ID: 23081826.
    Abstract:
    A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α-amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans-epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98%). The obtained epoxy amides were found to be useful as synthetic building blocks. Thus, they were reduced into their corresponding epoxy alcohols and subjected to oxirane-ring-opening reactions with different types of nucleophiles.
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