Synlett

Behaviour of Dioxolanones as Chiral Acyl Anion Equivalents

RA Aitken, AW Thomas

Index: Aitken, R. Alan; Thomas, Andrew W. Synlett, 1998 , # 1 p. 102 - 104

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Citation Number: 17

Abstract

Abstract: The 1, 3-dioxolan-4-ones readily derived from α-hydroxy acids act as convenient acyl anion equivalents by deprotonation–alkylation followed by flash vacuum pyrolysis. Conjugate addition of their anions to ethyl crotonate similarly gives β-methyl-γ-oxo esters and by using chiral dioxolanones these can be obtained in up to 86% ee

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