10.1021/ol0509080.s001 Mieczysław Ma̧kosza Mieczysław Ma̧kosza Michał Barbasiewicz Michał Barbasiewicz Dariusz Krajewski Dariusz Krajewski Diastereoselective Synthesis of Tetrahydrofurans via Reaction of γ,δ-Epoxycarbanions with Aldehydes<sup>†</sup> American Chemical Society 2005 adduct potassium tert presence butoxide Aldehyde oxirane ring Diastereoselective Synthesis S N 2 process carbanion Tetrahydrofuran cyclization Epoxycarbanion nondiastereoselective sulfone aldehyde diastereoisomer lithium mixture tetrahydrofuran phenyl diastereoselectivity epoxybutyl Initial formation configuration carbon stereocenter diastereoselectively 2005-07-07 00:00:00 Dataset https://acs.figshare.com/articles/dataset/Diastereoselective_Synthesis_of_Tetrahydrofurans_via_Reaction_of_Epoxycarbanions_with_Aldehydes_sup_sup_/3278557 Hydroxymethyl-substituted tetrahydrofurans were prepared with high diastereoselectivity by reaction of the carbanion derived from 3,4-epoxybutyl phenyl sulfone with aldehydes in the presence of a mixture of lithium and potassium <i>tert-</i>butoxides. Initial formation of aldol-type adducts is a nondiastereoselective but reversible process; thus, subsequent formation of one main diastereoisomer is controlled by the relative rates of cyclization. The configuration of the carbon stereocenter at the oxirane ring is inverted in the course of the S<sub>N</sub>2 process, and two new centers are created diastereoselectively.