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Journal Articles Angewandte Chemie International Edition Year : 2017

Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes

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Abstract

The first catalytic asymmetric synthesis of highly functionalized difluoromethylated cyclopropanes is described. The method, based on a rhodium‐catalyzed cyclopropanation of difluoromethylated olefins, gives access to a broad range of cyclopropanes bearing ester, ketone, or nitro functional groups. By using Rh2((S)‐BTPCP)4 as a catalyst, the corresponding products were obtained in high yields and high diastereo‐ and enantioselectivities (up 20:1 d.r. and 99 % ee). This methodology allowed preparation of enantioenriched difluoromethylcyclopropanes for the first time.
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hal-02046261 , version 1 (22-02-2019)

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Maxence Bos, Wei-Sheng Huang, Thomas Poisson, Xavier Pannecoucke, André B. Charette, et al.. Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes. Angewandte Chemie International Edition, 2017, 56 (43), pp.13319-13323. ⟨10.1002/anie.201707375⟩. ⟨hal-02046261⟩
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