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Highly efficient biocatalytic desymmetrization of meso carbocyclic 1,3-dicarboxamides: a versatile route for enantiopure 1,3-disubstituted cyclohexanes and cyclopentanes

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Abstract

A versatile biocatalytic desymmetric strategy for efficiently accessing enantiopure 1,3-disubstituted cyclohexanes and cyclopentanes was developed. Desymmetric hydrolysis of a series of meso carbocyclic 1,3-dicarboxamides catalyzed by Rhodococcus erythropolis AJ270 whole cells under mild conditions afforded 3-carbamoylcyclic carboxylic acid derivatives in 81–95% yields and >99.5% ee values. The desymmetrization of different types of substrates shows a general S-selectivity, and the catalytic efficiency and enantioselectivity show dependence on the cyclic structure of the substrates. The biocatalytic products were conveniently transformed to chiral bicyclic oxazolidinone compounds.

Graphical abstract: Highly efficient biocatalytic desymmetrization of meso carbocyclic 1,3-dicarboxamides: a versatile route for enantiopure 1,3-disubstituted cyclohexanes and cyclopentanes

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Publication details

The article was received on 16 Jan 2019, accepted on 04 Feb 2019 and first published on 04 Feb 2019


Article type: Research Article
DOI: 10.1039/C9QO00069K
Citation: Org. Chem. Front., 2019, Advance Article

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    Highly efficient biocatalytic desymmetrization of meso carbocyclic 1,3-dicarboxamides: a versatile route for enantiopure 1,3-disubstituted cyclohexanes and cyclopentanes

    H. Hu, P. Chen, Y. Ao, Q. Wang, D. Wang and M. Wang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00069K

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