STEREOSPECIFIC EPOXIDATION OF 4-HYDROXYCYCLOPENT-2-ENONES

Authors
DAURIA M PIANCATELLI G
Citation
M. Dauria et G. Piancatelli, STEREOSPECIFIC EPOXIDATION OF 4-HYDROXYCYCLOPENT-2-ENONES, Chemistry Letters, (7), 1993, pp. 1153-1156
Citations number
13
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
7
Year of publication
1993
Pages
1153 - 1156
Database
ISI
SICI code
0366-7022(1993):7<1153:SEO4>2.0.ZU;2-F
Abstract
The treatment of 4,5-dialkyl-4-hydroxy-6-cyclopent-2-en-1-ones with H2 O2 and KOH gave in high yields 2,3-epoxy-2,3-dialkyl-4-hydroxycyclopen tanones. Furthermore, only one stereoisomer, characterized by trans re lationship between the hydroxy group and the epoxide was obtained. Thi s behaviour can be explained considering that epoxidation occurs durin g a base catalyzed transposition of the starting cyclopentenone.