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标题：Regiodivergent and stereoselective hydroxyazidation of alkenes by biocatalytic cascades
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作者：Jing-Fei Wu ; Nan-Wei Wan ; Ying-Na Li 等
期刊名称：iScience
印刷版ISSN：2589-0042
出版年度：2021
卷号：24
期号：8
页码：1-23
DOI：10.1016/j.isci.2021.102883
语种：English
出版社：Elsevier
摘要：SummaryAsymmetric functionalization of alkenes allows the direct synthesis of a wide range of chiral compounds. Vicinal hydroxyazidation of alkenes provides a desirable path to 1,2-azidoalcohols; however, existing methods are limited by the control of stereoselectivity and regioselectivity. Herein, we describe a dual-enzyme cascade strategy for regiodivergent and stereoselective hydroxyazidation of alkenes, affording various enantiomerically pure 1,2-azidoalcohols. The biocatalytic cascade process is designed by combining styrene monooxygenase-catalyzed asymmetric epoxidation of alkenes and halohydrin dehalogenase-catalyzed regioselective ring opening of epoxides with azide. Additionally, a one-pot chemo-enzymatic route to chiralβ-hydroxytriazoles from alkenes is developed via combining the biocatalytic cascades and Cu-catalyzed azide-alkyne cycloaddition.Graphical abstractDisplay OmittedHighlights•A dual-enzyme cascade is developed for asymmetric hydroxyazidation of alkenes•Regiodivergent and stereoselective hydroxyazidation of alkenes is achieved•Various enantiomerically pure 1,2-azidoalcohols are synthesized from alkenes•Chiralβ-hydroxytriazoles are prepared from alkenes by a chemo-enzymatic approachBiosynthesis; Biocatalysis ; Bioengineering