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Ma, Hui-Chao; Chen, Gong-Jun; Huang, Fang; Dong, Yu-Bin
Journal of the American Chemical Society, 07/2020, Letnik: 142, Številka: 29Journal Article
( )-2-(2-Chlorophenyl)-2-(6,7-dihydrothieno3,2- pyridin-5(4 )-yl)acetonitrile (( )- ) is a key intermediate in the synthesis of ( )-clopidogrel, which is one of the most saleable worldwide antiplatelet and antithrombotic drugs. We show herein a facile method for the direct synthesis of ( )- 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 ( )- 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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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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