Journal
ORGANIC LETTERS
Volume 24, Issue 1, Pages 293-298Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03950
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- Science and Technology Commission of Shanghai Municipality [21ZR1419300]
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The divergent chemoselective synthesis of 2-methylene-2,3-dihydrothiazoles and 4-benzylidene pyrrolidine-2-thiones (most with E stereoselectivity) from N-propargyl thiocarbamoyl fluorides and malonate esters has been accomplished, with one pathway providing 4-benzylidene pyrrolidine-2-thiones and another leading to 2-methylene-2,3-dihydrothiazoles through isomerization of alpha,alpha-diester thioamide intermediates.
The divergent chemoselective synthesis of 2-methylene-2,3-dihydrothiazoles and 4-benzylidene pyrrolidine-2-thiones (most with E stereoselectivity) from N-propargyl thiocarbamoyl fluorides and malonate esters in moderate to excellent yields with a broad substrate scope and functional group tolerance has been accomplished. AgNTf2 catalyst at 60 degrees C in dichloroethane provided 4-benzylidene pyrrolidine-2-thiones. AgOTf catalyst and PPh3 ligand in refluxing acetonitrile resulted in a complete switch in the reactivity of formed alpha,alpha-diester thioamide intermediates followed by isomerization to access 2-methylene-2,3-dihydrothiazoles.
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