Oxidative reactions of sulfinyl dienes as an entry to functionalized carbohydrate-like products and furans. Issue 32 (9th August 2019)

• Record Type: Journal Article
• Authors: Castellanos, Alejandro; Osante, Iñaki; Fernández, Jorge; Fernández de la Pradilla, Roberto; Viso, Alma
• Is Part Of: Tetrahedron. Volume 75:Issue 32(2019)
• Page Start: 4287
• Page End: 4297
• Publication Date: 2019-08-09
• Subjects: Sulfoxides -- Pyranoses -- Furans -- Oxidation -- Sulfones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.04.014
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Oxidative cleavage (OsO4 /NaIO4 ) of a monoprotected dihydroxy sulfinyl diene affords a lactol, readily transformed into a sulfinyl pyranose. Alternatively, base promoted intramolecular cyclization of a lactol derived carbamate to a bicyclic oxazolidinone followed by simple transformations leads to an amino sulfonyl pyranose. In contrast, ozonolysis of a variety of hydroxy sulfinyl dienes leads to fair yields of 3-sulfinyl furans in a single step. Graphical abstract: Image 1