ZINC-DIETHYLALUMINUM CHLORIDE-INDUCED COUPLING REACTION OF DIBROMOFLUOROACETATE WITH CARBONYL-COMPOUNDS - NEW EFFICIENT AND SELECTIVE SYNTHESIS OF ALPHA-BROMO-ALPHA-FLUORO-BETA-HYDROXY AND ALPHA-FLUORO-BETA'-DIHYDROXY ESTERS

Authors
ISHIHARA T MATSUDA T IMURA K MATSUI H YAMANAKA H
Citation
T. Ishihara et al., ZINC-DIETHYLALUMINUM CHLORIDE-INDUCED COUPLING REACTION OF DIBROMOFLUOROACETATE WITH CARBONYL-COMPOUNDS - NEW EFFICIENT AND SELECTIVE SYNTHESIS OF ALPHA-BROMO-ALPHA-FLUORO-BETA-HYDROXY AND ALPHA-FLUORO-BETA'-DIHYDROXY ESTERS, Chemistry Letters, (11), 1994, pp. 2167-2170
Citations number
23
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
11
Year of publication
1994
Pages
2167 - 2170
Database
ISI
SICI code
0366-7022(1994):11<2167:ZCCROD>2.0.ZU;2-M
Abstract
Treatment of ethyl dibromofluoroacetate with aldehydes or ketone in th e presence of zinc and diethylaluminium chloride at -20 degrees C gave rise to the corresponding alpha-bromo-alpha-fluoro-beta-hydroxy alkan oic acid ethyl esters in good yields, while the use of two equivalents each of aldehyde, zinc, and diethylaluminium chloride in the reaction resulted in a double coupling reaction affording the 1:2 adducts, alp ha-fluoro-beta,beta>'-dihydroxy esters in high yields.