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.
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.
Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, 563000, China. yzchen@zmc.edu.cn.
Ke
K
Li
Juxiang
J
Wang
Kailin
K
Wu
Daijun
D
Zheng
Xiaojian
X
Zhou
Wenyong
W
Han
Nanwei
N
Wan
Baodong
B
Cui
Yongzheng
Y
Chen
D055162:Biocatalysis; D060326:Chemistry Techniques, Synthetic; D006900:Hydroxylation; D010084:Oxidation-Reduction; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D016929:Rhodococcus equi / Q000378:metabolism*; D013237:Stereoisomerism
D011804:Quinolines