Sulfenofunctionalization of Chiral α-Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF₃ , SCF₂ R, SCN and SAr Compounds.

ABSTRACT: We report herein a new method for the synthesis of densely functionalized chiral allyl SCF₃ , SCF₂ R, SCN and SAr species with a separate CF₃ functionality. The synthetic approach is based on selenium-catalyzed sulfenofunctionalization of chiral α-CF₃ allylboronic acids. The reactions proceeded with remarkably high stereo-, diastereo- and site-selectivity, based on the formation of a stable thiiranium ion followed by rapid deborylative ring opening.

SUBMITTER: Wang Q 

PROVIDER: S-EPMC9828052 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature