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Issue 3, 2019
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Rhodium catalysed enantioselective synthesis of mono-(halo)-methyl-cyclopropanes

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Abstract

The catalytic asymmetric synthesis of mono-fluoro-, -chloro- and -bromomethyl-1,2-diaryl cyclopropane ester is described. The reaction, using Rh2((S)-BTPCP)4 as a catalyst, allowed the formation of the desired cyclopropanes in good to excellent yields (up to 99%) and excellent diastereoselectivities (up to >20 : 1) and with a high level of enantioselectivities (up to 98% ee). Finally, the synthetic utility of the chiral cyclopropanes was also demonstrated.

Graphical abstract: Rhodium catalysed enantioselective synthesis of mono-(halo)-methyl-cyclopropanes

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Publication details

The article was received on 06 Dec 2018, accepted on 12 Dec 2018 and first published on 12 Dec 2018


Article type: Communication
DOI: 10.1039/C8OB03041C
Citation: Org. Biomol. Chem., 2019,17, 472-476
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    Rhodium catalysed enantioselective synthesis of mono-(halo)-methyl-cyclopropanes

    C. Schlinquer, W. Huang, L. Chen, T. Poisson, X. Pannecoucke, A. B. Charette and P. Jubault, Org. Biomol. Chem., 2019, 17, 472
    DOI: 10.1039/C8OB03041C

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