Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 6, Issue 6, Pages 808-812Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9qo00069k
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Funding
- National Natural Science Foundation of China [21502202, 21521002]
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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.
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