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Synlett 1998; 1998(1): 102-104
DOI: 10.1055/s-1998-1569
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Behaviour of Dioxolanones as Chiral Acyl Anion Equivalents

R. Alan Aitken* , Andrew W. Thomas
  • *School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK; Fax +44 (0) 13 34 46 38 08; E-mail: raa@st-and.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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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% e.e.

chiral acyl anion equivalents - 1,3-dioxolan-4-ones - flash vacuum pyrolysis - asymmetric synthesis

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