The intramolecular addition reaction of metal enolates of ketones to oxiranes has been applied to a series of epoxy ketones derived from cyclohexene oxide. γ-Hydroxy ketones (γ-HKs, C-alkylation products) or hydroxy enol ethers (HEEs, O-alkylation products) are obtained, depending on the nature of the cyclic transition state in each case involved and the application of the Fürst-Plattner rule. The formation of HEEs by reaction of the same epoxy ketones under acid conditions is also described. In some cases, regioconvergent or chemoselective processes are conveniently obtained. © 2001 Elsevier Science Ltd. All rights reserved.
|Autori:||P. CROTTI; F. BADALASSI; V. DI BUSSOLO; L. FAVERO; M. PINESCHI|
|Titolo:||Stereo- and regioselectivity of cyclization reactions in conformationally restricted epoxy ketones: evaluation of C-versus O-alkylation process|
|Anno del prodotto:||2001|
|Digital Object Identifier (DOI):||10.1016/S0040-4020(01)00817-1|
|Appare nelle tipologie:||1.1 Articolo in rivista|