Sulfenofunctionalization of Chiral α‐Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF<sub>3</sub>, SCF<sub>2</sub>R, SCN and SAr Compounds
Qiang Wang, Tomas Nilsson, Lars Eriksson, Kálmán J. Szabó
Abstract
Abstract We report herein a new method for the synthesis of densely functionalized chiral allyl SCF 3 , SCF 2 R, SCN and SAr species with a separate CF 3 functionality. The synthetic approach is based on selenium‐catalyzed sulfenofunctionalization of chiral α‐CF 3 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.
Topics & Concepts
TrifluoromethylChemistryComputational chemistryCombinatorial chemistryStereochemistryOrganic chemistryAlkylFluorine in Organic ChemistryCarbohydrate Chemistry and SynthesisSulfur-Based Synthesis Techniques