Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 2053-2056 |
| Seitenumfang | 4 |
| Fachzeitschrift | Liebigs Annalen |
| Jahrgang | 1995 |
| Ausgabenummer | 11 |
| Publikationsstatus | Veröffentlicht - 24 Okt. 1995 |
| Extern publiziert | Ja |
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.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Allgemeine Chemie
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in: Liebigs Annalen, Jahrgang 1995, Nr. 11, 24.10.1995, S. 2053-2056.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - 3,4‐bis(O‐tert‐butyldimethylsilyl)‐6‐O‐tosyl‐D‐glucal
T2 - A probe for the mechanism of the iodine(III)‐promoted allylic oxidation of glycals
AU - Kirschning, Andreas
PY - 1995/10/24
Y1 - 1995/10/24
N2 - 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.
AB - 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.
KW - 2,3‐Anhydropyranose
KW - Glycal
KW - Hypervalent iodine
UR - http://www.scopus.com/inward/record.url?scp=84988129725&partnerID=8YFLogxK
U2 - 10.1002/jlac.1995199511289
DO - 10.1002/jlac.1995199511289
M3 - Article
AN - SCOPUS:84988129725
VL - 1995
SP - 2053
EP - 2056
JO - Liebigs Annalen
JF - Liebigs Annalen
SN - 0947-3440
IS - 11
ER -