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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

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Sulfenofunctionalization of Chiral α-Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF<sub>3</sub> , SCF<sub>2</sub> R, SCN and SAr Compounds.

Wang Qiang Q   Nilsson Tomas T   Eriksson Lars L   Szabó Kálmán J KJ  

Angewandte Chemie (International ed. in English) 20221017 46

We report herein a new method for the synthesis of densely functionalized chiral allyl SCF<sub>3</sub> , SCF<sub>2</sub> R, SCN and SAr species with a separate CF<sub>3</sub> functionality. The synthetic approach is based on selenium-catalyzed sulfenofunctionalization of chiral α-CF<sub>3</sub> 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. ...[more]

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