Asymmetric Synthesis of β-Ketoamides by Sulfonium Rearrangement.

ABSTRACT: The synthesis of enantioenriched α-substituted 1,3-dicarbonyls remains a contemporary challenge in synthesis due to their tendency to undergo racemization via keto-enol tautomerization. Herein, we report a method to access enantioenriched β-ketoamides by a chiral sulfinimine-mediated [3,3]-sigmatropic sulfonium rearrangement. The transformation displays good chirality transfer, as well as excellent chemoselectivity and functional group tolerance. Diastereoselective reduction of the ketone moiety, also achievable in one-pot fashion, affords enantioenriched β-hydroxyamides.

SUBMITTER: Porte V 

PROVIDER: S-EPMC11627135 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature