Stereo- and regioselectivity of cyclization reactions in conformationally restricted epoxy ketones: evaluation of C- versus O-alkylation process

Authors
Crotti, P Badalassi, F Di Bussolo, V Favero, L Pineschi, M
Citation
P. Crotti et al., Stereo- and regioselectivity of cyclization reactions in conformationally restricted epoxy ketones: evaluation of C- versus O-alkylation process, TETRAHEDRON, 57(40), 2001, pp. 8559-8572
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
40
Year of publication
2001
Pages
8559 - 8572
Database
ISI
SICI code
0040-4020(20011001)57:40<8559:SAROCR>2.0.ZU;2-#
Abstract
The intramolecular addition reaction of metal enolates of ketones to oxiran es has been applied to a series of epoxy ketones derived from cyclohexene o xide. gamma -Hydroxy ketones (gamma -HKs, C-alkylation products) or hydroxy enol ethers (HEEs, O-alkylation products) are obtained, depending on the n ature of the cyclic transition state in each case involved and the applicat ion of the Furst-Plattner rule. The formation of HEEs by reaction of the sa me epoxy ketones under acid conditions is also described. In some cases, re gioconvergent or chemoselective processes are conveniently obtained. (C) 20 01 Elsevier Science Ltd. All rights reserved.