The regiochem. outcome of the ring-opening of epoxides bearing remote polar functionalities was established in the case of carbocyclic and furanosidic epoxides I (X = O, CH2). Under std. conditions, the regioisomeric C(1) products are the sole (from trans epoxides) or predominant (from cis epoxides) ring-opening products. However, under chelating conditions, and only in the case of the cis epoxides, a consistent increase in C(2) selectivity is unexpectedly obsd.
|Autori:||CROTTI P; V. DI BUSSOLO; L. FAVERO; F. MACCHIA; M.PINESCHI|
|Titolo:||Regiochemical Control of the Ring Opening of Epoxides by Means of Chelating Processes. 13. Synthesis and Ring-Opening Reactions of the Distereoisomeric cis- and trans Epoxides Derived from 3-(Benzyloxy)cyclopentene and 2-(Benzyloxy)-2,5-dihydrofuran|
|Anno del prodotto:||1998|
|Digital Object Identifier (DOI):||10.1002/(SICI)1099-0690(199808)1998:8<1675::AID-EJOC1675>3.0.CO;2-B|
|Appare nelle tipologie:||1.1 Articolo in rivista|