Download PDF
Synlett 1998; 1998(1): 102-104
DOI: 10.1055/s-1998-1569
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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