Enantiopure cis- and trans-2, 5-disubstituted-2, 5-dihydrofurans from d-allal- and d-galactal-derived vinyl epoxides. Issue 33 (16th August 2019)

• Record Type: Journal Article
• Authors: Di Bussolo, Valeria; Princiotto, Salvatore; Bordoni, Vittorio; Martinelli, Elisa; Favero, Lucilla; Crotti, Stefano; Uccello Barretta, Gloria; Balzano, Federica; Pineschi, Mauro; Crotti, Paolo
• Is Part Of: Tetrahedron. Volume 75:Issue 33(2019)
• Page Start: 4425
• Page End: 4443
• Publication Date: 2019-08-16
• Subjects: Vinyl epoxides -- Glycals -- 2, 5-Disubstituted-2, 5-dihydrofurans -- Rearrangement process -- Stereoselectivity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.06.003
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Upon treatment with the metal enolates of methylene active compounds (dimethyl malonate and dibenzoylmethane) ( C -nucleophiles) and benzyl carbamate ( N -nucleophile), d -allal- andd -galactal-derived vinyl epoxides are stereoselectively transformed, in a single step, into diastereoisomeric, highly functionalized, enantiopure cis - and trans -2, 5-disubstituted-2, 5-dihydrofurans. Graphical abstract: Image 1