4.0 Article

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

Journal

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
Volume 110, Issue -, Pages 87-91

Publisher

ELSEVIER SCIENCE BV
DOI: 10.1016/j.molcatb.2014.09.013

Keywords

Asymmetric synthesis; Enzyme catalysis; Oxidation; Chiral sce-alcohols; Pseudomonas plecoglossicidas

Funding

  1. Education Department of Guizhou Province [QSZHZ-2012-169, QJHRCTDZ-2012-03]
  2. Science and Technology Department of Guizhou Province [QKHGZ-2012-3078, QKHRZ-2013-47, QKHRCTD-2014-4002]
  3. National Nature Science Foundation of China (NSFC) [21162047, 21262051]
  4. New Century Excellent Talent of the Ministry of Education [NCET-13-1069]

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Two whole-cell biocatalysts were found to have C-H oxidation activity with high R-enantioselectivity on 1,2,3,4-tetrahydroquinoline (THQ) and 2,3,4,5-tetrahydro-1H-benzo[b]azepine (TBA). R-1,2,3,4-tetrahydroquinolin-4-ol ((R)-THQL) and R-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ol ((R)-TBAL) were smoothly obtained with 82% yield in 99% e.e. and 99% yield in 98% e.e., respectively. (C) 2014 Elsevier B.V. All rights reserved.

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