通过马红球菌ZMU-LK19的顺序不对称羟基化/非对映选择性氧化过程对1,2,3,4-四氢喹啉-4-醇和2,3-二氢喹啉-4(1H)-酮进行对映选择性合成。

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.

作者信息

Li Ke, Wang Juxiang, Wu Kailin, Zheng Daijun, Zhou Xiaojian, Han Wenyong, Wan Nanwei, Cui Baodong, Chen Yongzheng

机构信息

Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, 563000, China.

出版信息

Org Biomol Chem. 2017 May 3;15(17):3580-3584. doi: 10.1039/c7ob00151g.

DOI:10.1039/c7ob00151g

PMID:28177033

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.

摘要

利用马红球菌ZMU-LK19构建了一个涉及不对称羟基化和非对映选择性氧化的级联生物催化体系，该体系可从（±）-2-取代四氢喹啉（1）制备手性2-取代-1,2,3,4-四氢喹啉-4-醇（2）（分离产率高达57%，非对映体比例为99:1，对映体过量值>99%）和手性2-取代-2,3-二氢喹啉-4（1H）-酮（3）（分离产率高达25%，对映体过量值>99%）。此外，还初步提出了这种级联生物催化的可能机制。