Zinc-Diethylaluminium Chloride Induced Coupling Reaction of Dibromofluoroacetate with Carbonyl Compounds. New Efficient and Selective Synthesis of α-Bromo-α-fluoro-β-hydroxy and α-Fluoro-β,β′-dihydroxy Esters
- 1 November 1994
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 23 (11) , 2167-2170
- https://doi.org/10.1246/cl.1994.2167
Abstract
Treatment of ethyl dibromofluoroacetate with aldehydes or ketone in the presence of zinc and diethylaluminium chloride at −20 °C gave rise to the corresponding α-bromo-α-fluoro-β-hydroxy alkanoic 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, α-fluoro-β,β′-dihydroxy esters in high yields.Keywords
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