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Homochiral Covalent Organic Framework for Catalytic Asymmetric Synthesis of a Drug Intermediate.
J Am Chem Soc. 2020 Jul 22; 142(29):12574-12578.JA

Abstract

(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.

Authors+Show Affiliations

College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, P. R. China.College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, P. R. China.College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, P. R. China.College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan 250014, P. R. China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32574049

Citation

Ma, Hui-Chao, et al. "Homochiral Covalent Organic Framework for Catalytic Asymmetric Synthesis of a Drug Intermediate." Journal of the American Chemical Society, vol. 142, no. 29, 2020, pp. 12574-12578.
Ma HC, Chen GJ, Huang F, et al. Homochiral Covalent Organic Framework for Catalytic Asymmetric Synthesis of a Drug Intermediate. J Am Chem Soc. 2020;142(29):12574-12578.
Ma, H. C., Chen, G. J., Huang, F., & Dong, Y. B. (2020). Homochiral Covalent Organic Framework for Catalytic Asymmetric Synthesis of a Drug Intermediate. Journal of the American Chemical Society, 142(29), 12574-12578. https://doi.org/10.1021/jacs.0c04722
Ma HC, et al. Homochiral Covalent Organic Framework for Catalytic Asymmetric Synthesis of a Drug Intermediate. J Am Chem Soc. 2020 Jul 22;142(29):12574-12578. PubMed PMID: 32574049.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Homochiral Covalent Organic Framework for Catalytic Asymmetric Synthesis of a Drug Intermediate. AU - Ma,Hui-Chao, AU - Chen,Gong-Jun, AU - Huang,Fang, AU - Dong,Yu-Bin, Y1 - 2020/07/13/ PY - 2020/6/24/pubmed PY - 2020/6/24/medline PY - 2020/6/24/entrez SP - 12574 EP - 12578 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 142 IS - 29 N2 - (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. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/32574049/Homochiral_Covalent_Organic_Framework_for_Catalytic_Asymmetric_Synthesis_of_Drug_Intermediate L2 - https://doi.org/10.1021/jacs.0c04722 DB - PRIME DP - Unbound Medicine ER -
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