Oxidative decarboxylation of alcohol hemiacetals of .alpha.-keto carboxylic acids with N-iodosuccinimide

Abstract

Recently,1 we found that -hydroxy carboxylic acids were easily decarboxylated with JV-iodosuccinimide (NIS). At this time, we report that the methyl and ethyl alcohol hemiacetals of -keto carboxylic acids also give good yields of bond-cleavage products when treated with NIS. Similar oxidative cleavage of -keto carboxylic acid hemiacetals using lead tetracetate was observed by Baer,2 although the

Domino Reaction of Naphthoquinone and β‐Arylpyruvic Acids: Synthesis of 3‐(Naphthoquinonyl)naphthofuran‐2(3H)‐ones

“…A similar pathway can be proposed for the Fe(OAc) 2 ‐catalyzed process . An oxidative decarboxylation of alcohol hemiketals derived from α‐keto acids has been reported for the preparation of esters . Bode et al also postulated a possible oxidative decarboxylation mechanism of an α‐hemiaminal acid intermediate, in the chemoselective amide‐forming ligation of N ‐hydroxylamine derivatives with α‐keto acids .…”