Chiral sulfide and achiral sulfonic acid cocatalyzed enantioselective electrophilic tandem selenylation semipinacol rearrangement of allenols.

ABSTRACT: A highly enantioselective electrophilic selenylation/semipinacol rearrangement of allenols has been developed, which is enabled by the cooperative catalysis of a chiral sulfide and an achiral sulfonic acid. The designed and synthesized chiral sulfide catalyst and selenylating reagent play a crucial role in enhancing both enantioselectivity and reactivity. This approach exhibits excellent regio-, chemo-, and enantioselectivity, providing access to diverse enantioenriched cyclopentanones featuring an arylselenovinyl-substituted quaternary carbon stereocenter. Furthermore, these products can be transformed into synthetically valuable alkyne, vinyl bromide, and aniline derivatives. Mechanistic studies reveal that the combination of a chiral sulfide and an achiral sulfonic acid not only facilit

SUBMITTER: Cao RF 

PROVIDER: S-EPMC11876436 | biostudies-literature | 2025 Mar

REPOSITORIES: biostudies-literature