Easily accessible non-aromatic heterocycles with handles: 4-bromo-2,3-dihydrofurans from 1,2-dibromohomoallylic alcohols

Abstract

The first general preparation of 4-bromo-2,3-dihydrofurans is reported. These non-aromatic heterocyles containing a useful coupling handle are accessed via Cu-catalyzed intramolecular cyclization of 1,2-dibromohomoallylic alcohols, which are themselves available in...

Ring-Expansion Reactions of Epoxy Amides and Enamides: Functionalized Azetidines, Dihydrofurans, Diazocanes, or Dioxa-3-azabicyclonon-4-enes?

“…The importance of the azetidine scaffold is alluded to above, while the dioxa-3-azabicyclononene products are rather rare, and only a handful of aza-bicyclononene systems are known . The non-aromatic 2,3-dihydrofurans that also form part of this work are fairly common in nature and hence are important synthetic targets Structural characterization of crystalline diazocane diol isomers (described earlier as an oily mixture) upon thermal treatment of N -oxiranylmethyl benzenesulfonamide. …”

“…The importance of the azetidine scaffold is alluded to above, while the dioxa-3-azabicyclononene products are rather rare, and only a handful of aza-bicyclononene systems are known . The non-aromatic 2,3-dihydrofurans that also form part of this work are fairly common in nature and hence are important synthetic targets …”