期刊
CHEMICAL SCIENCE
卷 9, 期 22, 页码 5052-5056出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc01561a
关键词
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资金
- Swiss National Science Foundation through the NCCR Molecular Systems Engineering
- JSPS Overseas research
Visible light-driven reduction of imines to enantioenriched amines in aqueous solution is demonstrated for the first time. Excitation of a new water-soluble variant of the widely used [Ir(ppy)(3)] (ppy = 2-phenylpyridine) photosensitizer in the presence of a cyclic imine affords a highly reactive alpha-amino alkyl radical that is intercepted by hydrogen atom transfer (HAT) from ascorbate or thiol donors to afford the corresponding amine. The enzyme monoamine oxidase (MAO-N-9) selectively catalyzes the oxidation of one of the enantiomers to the corresponding imine. Upon combining the photoredox and biocatalytic processes under continuous photo-irradiation, enantioenriched amines are obtained in excellent yields. To the best of our knowledge, this is the first demonstration of a concurrent photoredox- and enzymatic catalysis leading to a light-driven asymmetric synthesis of amines.
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