Bromolysis and iodolysis of alpha,beta-epoxycarboxylic acids in water catalyzed by indium halides.
The ring opening of alpha,beta-epoxycarboxylic acids by bromide and iodide ions has been efficiently carried out in water in high regio- and stereoselective fashion. The iodolysis of trans-beta-monoalkylated epoxycarboxylic acids at pH 4.0 was completely alpha-regioselective and anti diastereoselective. The InCl(3)-catalyzed iodolysis of a variety of alpha,beta-epoxycarboxylic acids at pH 1.5 gave the corresponding anti beta-iodohydrins in 88-95% yields. The one-pot synthesis of the alpha- and beta-hydroxyhexanoic acids, starting from the corresponding alpha,beta-epoxycarboxylic acid 1a by iodolysis followed by reduction of the resulting iodohydrins 4a and 4b by NaBH(4)-InCl(3) in water, has been performed.
Amantini
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Dipartimento di Chimica, Università di Perugia Via Elce di Sotto 8, I-06123 Perugia, Italy.
Fringuelli
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Pizzo
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Vaccaro
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