An enantioselective difunctionalization of activated alkynes using chiral sulfinamide reagents is developed. It is an atom and chirality transfer process that allows for the modular synthesis of optically active alpha-amino acid derivatives under mild conditions. The reaction proceeds through an acid-catalyzed [2,3]-sigmatropic rearrangement mechanism with predictable stereochemistry and a broad scope.
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Department of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, United StatesDepartment of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, United States
O'Donnell, Martin J.
Drew, Mark D.
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Department of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, United StatesDepartment of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, United States
Drew, Mark D.
Cooper, Jeremy T.
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Department of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, United StatesDepartment of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, United States
Cooper, Jeremy T.
Delgado, Francisca
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Department of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, United StatesDepartment of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, United States
Delgado, Francisca
Zhou, Changyou
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Department of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, United StatesDepartment of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, United States