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.

Enantioselective Formal 1,2-Diamination of Ketenes with Iminosulfinamides: Asymmetric Synthesis of Unnatural α,α-Disubstituted α-Amino Acid Derivatives

“…Recently, the stereoselective [2,3]-sigmatropic rearrangement method has been utilized for the enantioselective amination of ynamides or α-alkyl-substituted amides (Scheme A). This process involves the formation of keteniminium ion intermediates through electrophilic activations (Scheme A, i and ii), followed by their trapping by sulfinamides with their sulfinyl oxygen atom.…”