Regio- and stereoselective benzylic hydroxylation to synthesize chiral tetrahydroquinolin-4-ol and tetrahydro-1H-benzo[b]azepin-5-ol with Pseudomonas plecoglossicidas》.pdf

Journal of Molecular Catalysis B: Enzymatic 110 (2014) 87–91 Contents lists available at ScienceDirect Journal of Molecular Catalysis B: Enzymatic j o u r na l h o me p a g e : w w w. elsev /locate/molc atb Regio- and stereoselective benzylic hydroxylation to synthesize chiral tetrahydroquinolin-4-ol and tetrahydro-1H-benzo[b]azepin-5-ol with Pseudomonas plecoglossicida s Daijun Zheng, Min Yang, Junrui Zhuo, Ke Li, Hongyan Zhang, Jiawei Yang, Baodong Cui, Yongzheng Chen ∗ School of Pharmacy, Zunyi Medical University, 201 Dalian Road, Zunyi 563000, PR China a r t i c l e i n f o a b s t r a c t Article history: Two whole-cell biocatalysts were found to have C–H oxidation activity with high R-enantioselectivity Received 9 July 2014 on 1,2,3,4-tetrahydroquinoline (THQ) and 2,3,4,5-tetrahydro-1H-benzo[b]azepine (TBA). R-1,2,3,4- Received in revised form tetrahydroquinolin-4-ol ((R)-THQL) and R-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ol ((R)-TBAL) were 15 September 2014 smoothly obtained with 82% yield in 99% e.e. and 99% yield in 98% e.e., respectively. Accepted 22 September 2014 © 2014 Elsevier B.V. All rights reserved. Available online 2 October 2014 Keywords: Asymmetric synthesis Enzyme catalysis Oxidation Chiral sce-alcohols Pseudomonas plecoglossicidas 1. Introduction brønsted acid binary system through consecutive intramolecular