Synthesis

2, 2-Dimethyl-1, 3-oxathiane 3, 3-dioxide: a γ-hydroxypropyl anion equivalent

K Fuji, Y Usami, Y Kiryu, M Node

Index: Fuji; Usami; Kiryu; Node Synthesis, 1992 , # 9 p. 852 - 858

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Citation Number: 3

Abstract

The reaction of4-lithio-2, 2-dimethyl-1, 3-oxathiane 3, 3-dioxide with various electrophiles is presented. Acylation of the anion provided labile 4-acyl-2, 2-dimethyl-1, 3-oxathiane 3, 3- dioxides which underwent desulfonation with silica gel to produce y-hydroxy ketones with three carbon unit elongation. Thus, 4-lithio-2, 2-dimethyl-1, 3-oxathiane 3, 3-dioxide was shown to be a useful synthetic equivalent of a y-hydroxypropyl anion. Methyl esters ...