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Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes

Maxence Bos 1 Wei-Sheng Huang 1 Thomas Poisson 1 Xavier Pannecoucke 1 André B. Charette Philippe Jubault 1
1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
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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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046261
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:39:30 PM
Last modification on : Tuesday, November 3, 2020 - 9:50:05 AM

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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, Wiley-VCH Verlag, 2017, 56 (43), pp.13319-13323. ⟨10.1002/anie.201707375⟩. ⟨hal-02046261⟩

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