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

• Published in: Angewandte Chemie International Edition Vol. 61; no. 46; p. e202210509
• Main Authors: Wang, Qiang, Nilsson, Tomas, Eriksson, Lars, Szabó, Kálmán J
• Format: Journal Article
• Language: English
• Published: 14-11-2022
• ISSN: 1521-3773; 1521-3773
• DOI: 10.1002/anie.202210509

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.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.