ChemInform Abstract: Synthesis of γ‐Difluoromethyl α,β‐Unsaturated γ‐Butyrolactones Using PhSCF₂SiMe₃ as a Difluoromethylating Agent.

Abstract

Synthesis of -Difluoromethyl ,-Unsaturated -Butyrolactones Using PhSCF 2SiMe3 as a Difluoromethylating Agent. -Suitable approaches to the desired title compounds are elaborated and the way via key lactol (II), obtained as diastereomeric mixture after SiO 2 chromatography, is found to be the optimal one. Both isomers of (II) react stereoselectively with Grignard reagents to produce butyrolactones of type (IV) as single isomers. Reduction of (II) affords exclusively product (VI). Finally, flash vacuum pyrolysis of these adducts produces the target lactones as interesting synthons of fluoro-containing systems. -(ISSAREE, A.; MASUSAI, C.; SOORUKRAM, D.; KUHAKARN, C.; REUTRAKUL, V.; POHMAKOTR*, M.; Eur. J. Org. Chem. 2015, 17, 3751-3759, http://dx.