title: Stereoselective Synthesis of Z-α,β-Unsaturated Sulfones Using Peterson Reagents.
abstract: New Peterson reagents were prepared by introducing alkyloxy groups on the silicon atom in order to fix the conformation of the sulfone anion. The reagents 1d and 1e reacted with a variety of aldehydes after the treatment with Li-base to give Z-α,β-unsaturated sulfones with up to >99:1 selectivity in good to excellent yields. For the reaction with aliphatic aldehydes, CPME (cyclopentyl methyl ether) is the choice of solvent, while DME (1,2-dimethoxyethane) gave higher selectivity for the reaction with aromatic aldehydes.
authors.affiliation: Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.
authors.forename: Kaori
authors.initials: K
authors.lastname: Ando
authors.affiliation: Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Wada
authors.affiliation: Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.
authors.forename: Miho
authors.initials: M
authors.lastname: Okumura
authors.affiliation: Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sumida