Acid-Catalyzed Highly Enantioselective Synthesis of α-Amino Acid Derivatives from Sulfinamides and Alkynes.

ABSTRACT

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 α-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.