Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes
Maxence Bos1,2, Wei-Sheng Huang1, Thomas Poisson1
1Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France.
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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