Oxidative reactions of sulfinyl dienes as an entry to functionalized carbohydrate-like products and furans

TETRAHEDRON

卷:75

Article

Castellanos, Alejandro¹  Osante, Inaki¹  Fernandez, Jorge¹  Fernandez de la Pradilla, Roberto¹  Viso, Alma¹ 

[1] CSIC, Inst Quim Organ Gen, Juan Cierva 3, E-28006 Madrid, Spain

关键词: Sulfoxides;    Pyranoses;    Furans;    Oxidation;    Sulfones;   

DOI  :  10.1016/j.tet.2019.04.014

来源: Elsevier

【 摘 要 】

Oxidative cleavage (OsO4/NalO(4)) 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. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

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