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Ye, Qunqun; Cheng, Tanyu; Zhao, Yuxi; Zhao, Junwei; Jin, Ronghua; Liu, Guohua
ChemCatChem, 06/2015, Letnik: 7, Številka: 12Journal Article
The facile construction of biologically active beta-adrenergic receptor agonists/blockers and analogues is a great fundamental and practical challenge in medical chemistry. Herein, we report a hydration-asymmetric transfer hydrogenation cascade to realize the one-pot enantioselective transformation of aromatic haloalkynes into chiral aromatic halohydrins, which can be converted readily into chiral beta-adrenergicreceptor blockers. Such a one-pot cascade process involves the Au-catalyzed hydration of aryl-substituted haloalkynes to aryl-substituted alpha-halomethyl ketones and the Ru-catalyzed asymmetric transfer hydrogenation of aryl-substituted alpha-halomethyl ketones to aryl-substituted 2-haloethanols. The significant benefits of this procedure are that it provides chiral aromatic halohydrins in high yields, with excellent enantioselectivities, and a wide variety of functional groups are tolerated under mild conditions. The study described herein offers a useful approach to construct chiral beta-adrenergic blockers, which is an attractive practical organic transformation that is performed in a one-pot manner.
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