Diastereoselective cis to trans desymmetrization of dimethyl succinates

Authors
Michieletto, I Fabris, F De Lucchi, O
Citation
I. Michieletto et al., Diastereoselective cis to trans desymmetrization of dimethyl succinates, TETRAHEDR-A, 10(13), 1999, pp. 2505-2509
Citations number
48
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
13
Year of publication
1999
Pages
2505 - 2509
Database
ISI
SICI code
0957-4166(19990702)10:13<2505:DCTTDO>2.0.ZU;2-A
Abstract
Meso-succinates, readily available by Diels-Alder cycloaddition of dimethyl maleate or maleic anhydride followed by esterification, can be isomerized quantitatively from the cis to the trans isomers in the presence of lithium alkoxides. The reaction performed with enantiopure chiral lithium alkoxide s yields diastereomeric trans-succinates in good yield and selectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.