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General Catalytic Enantioselective Access to Monohalomethyl and Trifluoromethyl Cyclopropanes

Abstract : An efficient catalytic enantioselective access to chiral functionalized trifluoromethyl cyclopropanes from two classes of diazo compounds and α‐trifluoromethyl styrenes using Rh2((S)‐BTPCP)4 as a catalyst is described. This method provides an efficient and practical strategy for the synthesis of highly functionalized CF3‐cyclopropanes with excellent diastereoselectivities (up to 20:1) and enantioselectivities (up to 99 % ee). The depicted methodology represents, to date, the most efficient catalytic enantioselective method to access highly decorated chiral CF3‐cyclopropanes. Extension to chiral monohalomethyl cyclopropanes in high ee is also reported.
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Submitted on : Tuesday, February 19, 2019 - 11:09:50 AM
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Wei-Sheng Huang, Claire Schlinquer, Thomas Poisson, Xavier Pannecoucke, A.B. Charette, et al.. General Catalytic Enantioselective Access to Monohalomethyl and Trifluoromethyl Cyclopropanes. Chemistry - A European Journal, Wiley-VCH Verlag, 2018, 24 (41), pp.10339-10343. ⟨10.1002/chem.201802685⟩. ⟨hal-02024505⟩



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