Diastereoselective cyclopropanation of cyclic enones with methyl dichloroacetate anion

Authors
Escribano, A Pedregal, C Gonzalez, R Fernandez, A Burton, K Stephenson, GA
Citation
A. Escribano et al., Diastereoselective cyclopropanation of cyclic enones with methyl dichloroacetate anion, TETRAHEDRON, 57(46), 2001, pp. 9423-9427
Citations number
34
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
46
Year of publication
2001
Pages
9423 - 9427
Database
ISI
SICI code
0040-4020(20011112)57:46<9423:DCOCEW>2.0.ZU;2-I
Abstract
The reaction of alpha,beta -unsaturated cyclic ketones with methyl dichloro acetate anion in the presence of DBU leads to the corresponding bicyclic ch lorocyclopropanes in a highly diastereoselective fashion. In the cases of 2 -cyclopentenone and 2-cyclohexenone the reaction affords exclusively the en do-Cl isomer. (C) 2001 Elsevier Science Ltd. All rights reserved.