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

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 proceede...

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Detalles Bibliográficos
Autores principales: Wang, Qiang, Nilsson, Tomas, Eriksson, Lars, Szabó, Kálmán J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9828052/
https://www.ncbi.nlm.nih.gov/pubmed/36152310
http://dx.doi.org/10.1002/anie.202210509
Descripción
Sumario: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.

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