2024
DOI: 10.1021/acs.orglett.3c04158
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Acid-Catalyzed Highly Enantioselective Synthesis of α-Amino Acid Derivatives from Sulfinamides and Alkynes

Herui Liu,
Guangwu Sun,
Yuchao Zhang
et al.

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.

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“…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.…”
mentioning
confidence: 99%
“…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.…”
mentioning
confidence: 99%