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

authored by

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.

External Organisation(s)

Clausthal University of Technology

Type

Article

Journal

Liebigs Annalen

Volume

1995

Pages

2053-2056

No. of pages

4

ISSN

0947-3440

Publication date

24.10.1995

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

General Chemistry

Electronic version(s)

https://doi.org/10.1002/jlac.1995199511289 (Access: Unknown)