Asymmetric combinational "metal-biocatalytic system": One approach to chiral 2-subsituted-tetrahydroquinoline-4-ols towards two-step one-pot processes in aqueous media. Issue 23 (7th June 2017)

• Record Type: Journal Article
• Authors: Wang, Juxiang; Li, Ke; Zhou, Xiaojian; Han, Wenyong; Wan, Nanwei; Cui, Baodong; Wang, Huihui; Yuan, Weicheng; Chen, Yongzheng
• Is Part Of: Tetrahedron letters. Volume 58:Issue 23(2017)
• Page Start: 2252
• Page End: 2254
• Publication Date: 2017-06-07
• Subjects: Combinational catalysis -- Asymmetric transfer hydrogenation -- Asymmetric hydroxylation -- Rhodococcus equi ZMU-LK19 -- 2-Subsituted-tetrahydroquinoline-4-ols; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.04.074
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Asymmetric "metal-biocatalytic system". One-pot conversion of 2-subsituted-quinolines to 2-subsituted-tetrahydroquinoline-4-ols. Synthesis of chiral 2-subsituted-tetrahydroquinoline-4-ols in moderate to excellent results. Further illustrates the potentiality of chemoenzymatic multistep one-pot processes. Abstract: A novel asymmetric "metal-biocatalytic system", involving Rh-catalyzed asymmetric transfer hydrogenation and whole cell mediated asymmetric hydroxylation in aqueous buffer, has been achieved. The methodology gives access to 2-subsituted-tetrahydroquinoline-4-ols bearing two stereocenters from 2-subsituted-quinolines in moderate to excellent results (up to 47% yield, 99:1 dr, and >99% ee).