(-)-fenchone derived epoxy alcohols - preparation and configuration

Authors
Philipova, I Dimitrov, V Simova, S
Citation
I. Philipova et al., (-)-fenchone derived epoxy alcohols - preparation and configuration, TETRAHEDR-A, 10(5), 1999, pp. 913-921
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
5
Year of publication
1999
Pages
913 - 921
Database
ISI
SICI code
0957-4166(19990312)10:5<913:(DEA-P>2.0.ZU;2-C
Abstract
Several chiral diastereoisomerically pure epoxy alcohols were prepared dias tereoselectively in high yields after epoxidation of allyl and homoallyl al cohols containing the 1R-fenchone skeleton with VO(acac)(2)/t-butyl hydrope roxide. The configurations of some of the new chiral compounds were determi ned by NMR methods. An interesting rearrangement reaction of an epoxy alcoh ol to an olefinic diol catalyzed by V5+ ions was observed. (C) 1999 Elsevie r Science Ltd. All rights reserved.