Bicarbonate-binding catalysis for the enantioselective desymmetrization of keto sulfonium salts

José Alemán (), Jorge Humbrías-Martín, Roberto Río-Rodríguez, Fernando Aguilar-Galindo, Sergio Díaz-Tendero and Jose A. Fernández-Salas ()
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José Alemán: Universidad Autónoma de Madrid, Cantoblanco
Jorge Humbrías-Martín: Universidad Autónoma de Madrid, Cantoblanco
Roberto Río-Rodríguez: Universidad Autónoma de Madrid, Cantoblanco
Fernando Aguilar-Galindo: Universidad Autónoma de Madrid
Sergio Díaz-Tendero: Universidad Autónoma de Madrid
Jose A. Fernández-Salas: Universidad Autónoma de Madrid, Cantoblanco

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Herein, an enantioselective desymmetrization of cyclic keto sulfonium salts through enantioselective deprotonation/ring opening process by anion-binding catalysis is presented. We report a squaramide/HCO3- complex as catalytic active species which is able to stereo-differentiate two enantiomeric protons, triggering the ring opening event taking advantage of the great tendency of sulfonium salts to act as leaving groups. Thus, this desymmetrization methodology give rise to β-methylsulfenylated sulfa-Michael addition type products with excellent yields and very good enantioselectivities. The bifunctional organocatalyst has been demonstrated to be capable of activating simultaneously the base and the keto sulfonium salt by DFT calculations and experimental proofs.

Date: 2024
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DOI: 10.1038/s41467-024-48832-x

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