Sulfenofunctionalization of Chiral α‐Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF 3 , SCF 2 R, SCN and SAr Compounds

Sulfenofunctionalization of Chiral α‐Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF 3 , SCF 2 R, SCN and SAr Compounds

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 p...

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Bibliographic Details
Published in:Angewandte Chemie Vol. 134; no. 46
Main Authors: Wang, Qiang, Nilsson, Tomas, Eriksson, Lars, Szabó, Kálmán J.
Format: Journal Article
Language:English
Published: 14-11-2022
Online Access:Get full text
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Summary: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.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202210509