期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 29, 页码 12574-12578出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c04722
关键词
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资金
- NSFC [21971153, 21671122]
- Chang-Jiang Scholars Program of China
- Taishan Scholars Construction Project of Shandong Province
- Shandong Provincial Natural Science Foundation [ZR2018MB005]
(S)-2-(2-Chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetonitrile ((S)-CIK) is a key intermediate in the synthesis of (S)-clopidogrel, which is one of the most saleable worldwide antiplatelet and antithrombotic drugs. We show herein a facile method for the direct synthesis of (S)-CIK via Strecker reaction using a homochiral covalent framework catalyst in a heterogeneous way. The asymmetric synthesis involves a photothermal-conversion-triggered, thermally driven reaction which affords (S)-CIK in 98% yield with 94% enantiomeric excess under visible-light irradiation. Furthermore, the above approach is readily extended to a gram-scale level on a fixed-bed continuous-flow model reactor. The potential utility of this strategy is highlighted by the preparation of many more other types of chiral drugs and drug intermediates in a green and facile way.
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