Highly cis- or trans-selective oxygen to carbon rearrangements of anomerically linked 6-substituted tetrahydropyranyl enol ethers

Authors
Dixon, DJ Ley, SV Tate, EW
Citation
Dj. Dixon et al., Highly cis- or trans-selective oxygen to carbon rearrangements of anomerically linked 6-substituted tetrahydropyranyl enol ethers, J CHEM S P1, (19), 1999, pp. 2665-2667
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
19
Year of publication
1999
Pages
2665 - 2667
Database
ISI
SICI code
0300-922X(1999):19<2665:HCOTOT>2.0.ZU;2-S
Abstract
Low temperature Lewis acid catalysed oxygen to carbon rearrangements of ano merically linked 6-substituted tetrahydropyranyl enol ethers lead to the co rresponding trans-ketones in a highly diastereoselective manner, whereas at higher temperatures the cis-ketones are formed with a high degree of selec tivity under thermodynamic control.