FURTHER REARRANGEMENTS OF DIEPOXYCYCLOHEXANES - FORMATION OF ACETYLDIHYDROXYCYCLOPENTANE DERIVATIVES

Authors
MOSS GP KEAT OC BONDAR GV
Citation
Gp. Moss et al., FURTHER REARRANGEMENTS OF DIEPOXYCYCLOHEXANES - FORMATION OF ACETYLDIHYDROXYCYCLOPENTANE DERIVATIVES, Tetrahedron letters, 37(16), 1996, pp. 2877-2880
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
16
Year of publication
1996
Pages
2877 - 2880
Database
ISI
SICI code
0040-4039(1996)37:16<2877:FROD-F>2.0.ZU;2-R
Abstract
3,8-Dioxatricyclo[3.2.1.0(2,4)]octane derivatives are readily prepared by the Diels Alder reaction of furan followed by epoxidation, The oxy gen atoms are cis to each other and when treated with Lewis acids such as BF3 rearrange stereospecifically to give derivatives of acetyldihy droxycyclopentane with all five ring atoms chiral. Evidence for an eno l ether intermediate has been provided from the adduct using dimethyl acetylenedicarboxylate. Copyright (C) 1996 Elsevier Science Ltd.