Quick Search:

uzh logo
Browse by:
bullet
bullet
bullet
bullet

Zurich Open Repository and Archive

Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-19939

Satoh, H; Hutter, J; Luethi, H P; Manabe, S; Ishii, K; Ito, Y (2009). Low-Barrier Pathway for endo-Cleavage Induced Anomerization of Pyranosides with N-Benzyl-2,3-trans-oxazolidinone Groups. European Journal of Organic Chemistry, 2009(8):1127-1131.

[img] PDF (Verlags PDF) - Registered users only
1MB

View at publisher
[img] PDF (Authors manuscript) - Registered users only
1MB
[img] PDF (Additional Material) - Registered users only
1MB

Abstract

Pyranosides with N-benzyl-2,3-trans-oxazolidinone undergo anomerization from the beta form to the a form even in the presence of a weak Lewis acid. Experimental evidence for endocleavage, the breaking of the bond between the pyran-oxygen and anomeric carbon atoms, in the anomerization reactions was obtained. This unexpected phenomenon was investigated by quantum mechanical calculations, which found clear differences in the transition states between anomerized and non-anomerized substrates. The computations suggest that BF3 induces endo-cleavage followed by rotation of the C1-C2 bond to give the alpha form via lower-energy transition states.

Citations

Altmetrics

Downloads

1 download since deposited on 31 Jul 2009
0 downloads since 12 months

Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
DDC:540 Chemistry
Date:29 January 2009
Deposited On:31 Jul 2009 09:53
Last Modified:05 Jun 2014 13:50
Publisher:Wiley-Blackwell
ISSN:1099-0690
Publisher DOI:10.1002/ejoc.200801140

Users (please log in): suggest update or correction for this item

Repository Staff Only: item control page