3,4‐bis(O‐tert‐butyldimethylsilyl)‐6‐O‐tosyl‐D‐glucal

A probe for the mechanism of the iodine(III)‐promoted allylic oxidation of glycals

verfasst von

Andreas Kirschning

Abstract

The reaction of 3,4‐bis(O‐tert‐butyldimethylsilyl)‐6‐O‐tosyl‐D‐glucal 4 with the Koser reagent [PhI(OH)OTs] unexpectedly afforded tetrahydrofurfural 6 as well as 2,3‐anhydropyranose 7 as major products. This unprecedented, stereoselective transformation helps to gain further insight into the mechanism of the well‐documented hypervalent iodine‐promoted allylic oxidation of cyclic enol ethers. A novel chemoenzymatic method for the preparation of glucal 4 in high yield is presented.

Externe Organisation(en)

Technische Universität Clausthal

Typ

Artikel

Journal

Liebigs Annalen

Band

1995

Seiten

2053-2056

Anzahl der Seiten

4

ISSN

0947-3440

Publikationsdatum

24.10.1995

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Allgemeine Chemie

Elektronische Version(en)

https://doi.org/10.1002/jlac.1995199511289 (Zugang: Unbekannt)