ISSN:
0170-2041
Keywords:
Zinc enolates, thioalkylation of
;
Cyclopentanones, α-alkylidene
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
An α-alkylidation of cyclopentanone was achieved in two reaction steps in an overall yield of 20 to 79% via a zinc chloride-catalyzed thioalkylation of the zinc enolate of methyl 2-oxocyclopentanecarboxylate (3) and subsequent saponification/desulfurization of the β-(phenylthio) 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940908