A Highly Stereoselective Synthesis of Glycidic Amides Based on a New Class of Chiral Sulfonium Salts: Applications in Asymmetric Synthesis |
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| Authors: | Prof. Dr. Francisco Sarabia Carlos Vivar‐García Dr. Miguel García‐Castro Cristina García‐Ruiz Francisca Martín‐Gálvez Dr. Antonio Sánchez‐Ruiz Dr. Samy Chammaa |
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| Affiliation: | 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. |
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| Keywords: | amides asymmetric synthesis natural products oxiranes ylides |
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