Catalytic Asymmetric Synthesis of α,α-Difluoromethylated and α-Fluoromethylated Tertiary Alcohols

Wei-Sheng Huang (1) , Marie-Léonie Delcourt (1) , Xavier Pannecoucke (1) , André Charette (2) , Thomas Poisson (1, 3) , Philippe Jubault (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 CCVC - Centre In Green Chemistry and Catalysis [Montréal]
3 IUF - Institut universitaire de France

The catalytic asymmetric synthesis of α,α-difluoromethylated tertiary alcohols is described, using an asymmetric dihydroxylation reaction. This protocol using either the AD-mix-α or AD-mix-β allowed an easy access to these valuable fluorinated chiral building blocks, which have been obtained with excellent yields and er. In addition, the reaction was extended to the α-fluoromethylated analogues.

Domaines: Chimie

Wei-Sheng Huang, Marie-Léonie Delcourt, Xavier Pannecoucke, André Charette, Thomas Poisson, et al.. Catalytic Asymmetric Synthesis of α,α-Difluoromethylated and α-Fluoromethylated Tertiary Alcohols. Organic Letters, 2019, 21 (18), pp.7509-7513. ⟨10.1021/acs.orglett.9b02792⟩. ⟨hal-02282518⟩