A Highly Stereoselective Synthesis of Glycidic Amides Based on a New Class of Chiral Sulfonium Salts: Applications in Asymmetric Synthesis

Authors

  • Prof. Dr. Francisco Sarabia,

    Corresponding author
    1. Department of Organic Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n. 29071 Malaga (Spain), Fax: (+34) 952-131941
    • Department of Organic Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n. 29071 Malaga (Spain), Fax: (+34) 952-131941
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  • Carlos Vivar-García,

    1. Department of Organic Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n. 29071 Malaga (Spain), Fax: (+34) 952-131941
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  • Dr. Miguel García-Castro,

    1. Department of Organic Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n. 29071 Malaga (Spain), Fax: (+34) 952-131941
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  • Cristina García-Ruiz,

    1. Department of Organic Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n. 29071 Malaga (Spain), Fax: (+34) 952-131941
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  • Francisca Martín-Gálvez,

    1. Department of Organic Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n. 29071 Malaga (Spain), Fax: (+34) 952-131941
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  • Dr. Antonio Sánchez-Ruiz,

    1. Department of Organic Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n. 29071 Malaga (Spain), Fax: (+34) 952-131941
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  • Dr. Samy Chammaa

    1. Department of Organic Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n. 29071 Malaga (Spain), Fax: (+34) 952-131941
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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.

Abstract

Un nuevo tipo de sales de sulfonio quirales, caracterizadas por contener un sistema bicíclico, ha sido diseñado y sintetizado desde α-amino ácidos. Sus correspondientes iluros, preparados por tratamiento básico de las sales de sulfonio, reaccionaron suavemente con una amplia gama de aldehidos simples y quirales para dar las epoxiamidas trans en rendimientos desde razonables a muy buenos, y estereoselectividad excelente estimada en más de un 98 %. Las epoxiamidas obtenidas probaron ser útiles building blocks. Así, éstas fueron reducidas a sus correspondientes epoxialcoholes y, además, fueron sometidas a reacciones de apertura del anillo de oxirano con diferentes tipos de nucleófilos.

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