Hui‐Chao Ma, Gong‐Jun Chen, Fang Huang
Jun 23, 2020
Citations
0
Influential Citations
44
Citations
Journal
Journal of the American Chemical Society
Abstract
(S)-2-(2-Chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetonitrile ((S)-CIK) is a key intermediate to (S)-clopidogrel which is one of the most salable worldwide antiplatelet and antithrombotic drugs. We show herein a facile meth-od for direct synthesis of (S)-CIK via one-pot in situ Strecker reaction using homochiral covalent framework catalyst in a het-erogeneous way. The asymmetric synthesis herein 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 production 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.