Exceptionally mild, high-yield synthesis of alpha-fluoro acrylates.
Novel achiral and chiral alkyl alpha-(1,3-benzothiazol-2-ylsulfonyl)-alpha-fluoroacetates can be readily synthesized by metalation-fluorination of (1,3-benzothiazol-2-ylsulfonyl)acetates. DBU-mediated condensations of these fluorinated synthons with aldehydes proceed in a facile manner at 0 degrees C or at room temperature giving high yields of alpha-fluoro acrylates. Ketones are unreactive under these conditions. The presence of fluorine renders the synthon substantially more reactive compared to the unfluorinated analogue. Reactivity of alpha-(1,3-benzothiazol-2-ylsulfonyl)-alpha-fluoroacetate and the Horner-Wadsworth-Emmons reagent (EtO)2P(O)CHFCOOEt has also been compared.
Zajc
Barbara
B
Department of Chemistry, The City College and The City University of New York, 138th Street at Convent Avenue, New York, New York 10031, USA. barbaraz@sci.ccny.cuny.edu
Kake
Shivani
S
D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D013237:Stereoisomerism
D000179:Acrylates; D005461:Fluorine