title: 2,5-cis-2,3,5-Trisubstituted tetrahydrofurans from the diastereomixture of 2,4-disubstituted 1,3-dioxepins via stereomutation.
abstract: A diastereoselective ring contraction of the diastereomixture of 2,4-disubstituted 1,3-dioxepins to 2,5-cis-2,3,5-trisubstituted tetrahydrofurans was achieved using TfOH in DMF. The reaction appears to proceed via a chair-like transition state, in which stereomutation of the oxocarbenium occurred, followed by an aldol-type cyclization.
authors: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871, Japan.
authors: Ozora
authors: O
authors: Kubo
authors: Kenzo
authors: K
authors: Yahata
authors: Tomohiro
authors: T
authors: Maegawa
authors: Hiromichi
authors: H
authors: Fujioka
mesh_terms: D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D010082:Oxepins / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005663:Furans; D010082:Oxepins