1-Chloroalkyl p-tolyl sulfoxides as useful agents for homologation of carbonyl compounds: conversion of carbonyl compounds to. alpha.-hydroxy acids, esters, and …

T Satoh, K Onda, K Yamakawa

Index: Satoh, Tsuyoshi; Onda, Ken-ichi; Yamakawa, Koji Journal of Organic Chemistry, 1991 , vol. 56, # 13 p. 4129 - 4134

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Citation Number: 26

Abstract

One-carbon homologation of carbonyl compounds to a-hydroxy acids, esters, and amides by the use of 1-chloroalkyl p-tolyl sulfoxide as a hydroxycarbonyl anion equivalent is reported. Oxidation of the vinyl chlorides, the intermediates of the above-mentioned method, with osmium tetraoxide gives a, a'-dihydroxy ketones which are found in biologically active natural products such as cortisone and adriamycin.