SYNTHESIS AND RING-OPENING REACTIONS OF THE DIASTEREOISOMERIC CIS-EPOXIDE AND TRANS-EPOXIDE DERIVED FROM 3-(BENZYLOXY)CYCLOPENTENE AND 2-(BENZYLOXY)-2,5-DIHYDROFURAN

Authors
CROTTI P DIBUSSOLO V FAVERO L MACCHIA F PINESCHI M
Citation
P. Crotti et al., SYNTHESIS AND RING-OPENING REACTIONS OF THE DIASTEREOISOMERIC CIS-EPOXIDE AND TRANS-EPOXIDE DERIVED FROM 3-(BENZYLOXY)CYCLOPENTENE AND 2-(BENZYLOXY)-2,5-DIHYDROFURAN, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (8), 1998, pp. 1675-1686
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY → ACNP
ISSN journal
1434193X
Issue
8
Year of publication
1998
Pages
1675 - 1686
Database
ISI
SICI code
1434-193X(1998):8<1675:SARROT>2.0.ZU;2-B
Abstract
The regiochemical outcome of the ring-opening of epoxides bearing remo te polar functionalities has been established in the case of carbocycl ic (1 and 2) and the corresponding furanosidic (3 and 4) title epoxide s. Under standard conditions, the regioisomeric C-1 products are the s ole (from trans epoxides 2 and 4) or predominant (from cis epoxides 1 and 3) ring-opening products. However, under chelating conditions, and only in the case of the cis epoxides 1 and 3, a consistent increase i n C-2 selectivity is unexpectedly observed.