title: Synthesis of di-, tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization.
abstract: Oxetanes offer exciting potential as structural motifs and intermediates in drug discovery and materials science. Here an efficient strategy for the synthesis of oxetane rings incorporating pendant functional groups is described. A wide variety of oxetane 2,2-dicarboxylates were accessed in high yields, including functionalized 3-/4-aryl- and alkyl-substituted oxetanes and fused oxetane bicycles. Enantioenriched alcohols provided enantioenriched oxetanes with complete retention of configuration. The oxetane products were further derivatized, while the ring was maintained intact, thus highlighting their potential as building blocks for medicinal chemistry.
authors.affiliation: Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ (UK) http://www3.imperial.ac.uk/people/j.bull.
authors.forename: Owen A
authors.initials: OA
authors.lastname: Davis
authors.forename: James A
authors.initials: JA
authors.lastname: Bull
keywords: OH insertion; cyclization; diazo compounds; heterocycles; oxetanes