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Enantioselective synthesis of 1,2,3,4-tetrahydroquinoline-4-ols and 2,3-dihydroquinolin-4(1H)-ones via a sequential asymmetric hydroxylation/diastereoselective oxidation process using Rhodococcus equi ZMU-LK19

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Abstract

A cascade biocatalysis system involving asymmetric hydroxylation and diastereoselective oxidation was developed using Rhodococcus equi ZMU-LK19, which gave chiral 2-substituted-1,2,3,4-tetrahydroquinoline-4-ols (2) (up to 57% isolated yield, 99 : 1 dr, and >99% ee) and chiral 2-substituted-2,3-dihydroquinolin-4(1H)-ones (3) (up to 25% isolated yield, and >99% ee) from (±)-2-substituted-tetrahydroquinolines (1). In addition, a possible mechanism for this cascade biocatalysis was tentatively proposed.

Graphical abstract: Enantioselective synthesis of 1,2,3,4-tetrahydroquinoline-4-ols and 2,3-dihydroquinolin-4(1H)-ones via a sequential asymmetric hydroxylation/diastereoselective oxidation process using Rhodococcus equi ZMU-LK19

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Publication details

The article was received on 19 Jan 2017, accepted on 30 Jan 2017, published on 30 Jan 2017 and first published online on 30 Jan 2017


Article type: Communication
DOI: 10.1039/C7OB00151G
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Enantioselective synthesis of 1,2,3,4-tetrahydroquinoline-4-ols and 2,3-dihydroquinolin-4(1H)-ones via a sequential asymmetric hydroxylation/diastereoselective oxidation process using Rhodococcus equi ZMU-LK19

    K. Li, J. Wang, K. Wu, D. Zheng, X. Zhou, W. Han, N. Wan, B. Cui and Y. Chen, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00151G

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