THIOALKYLATION OF ENOLATES .4. ALPHA-ALKYLIDENECYCLOPENTANONES BY ALPHA-ALKYLIDATION OF METHYL 2-OXOCYCLOPENTANECARBOXYLATE

Authors
ARNECKE R GROTH U KOHLER T
Citation
R. Arnecke et al., THIOALKYLATION OF ENOLATES .4. ALPHA-ALKYLIDENECYCLOPENTANONES BY ALPHA-ALKYLIDATION OF METHYL 2-OXOCYCLOPENTANECARBOXYLATE, Liebigs Annalen der Chemie, (9), 1994, pp. 891-894
Citations number
30
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen der Chemie → ACNP
ISSN journal
01702041
Issue
9
Year of publication
1994
Pages
891 - 894
Database
ISI
SICI code
0170-2041(1994):9<891:TOE.AB>2.0.ZU;2-9
Abstract
An alpha-alkylidation of cyclopentanone was achieved in two reaction s teps in an overall yield of 20 to 79% via a zinc chloride-catalyzed th ioalkylation of the zinc enolate of methyl 2-oxocyclopentanecarboxylat e (3) and subsequent saponification/desfulforization of the beta-(phen ylthio) ketone intermediates 5. For the saponification/desulfurization step DABCO proved to be the reagent of choice and superior to the use of alkali or magnesium halides.