Lithiated (E)-5-tosyl-4-pentenoic acid: A new delta-acyldienyl anion equivalent

Authors
Caturla, F Najera, C Varea, M
Citation
F. Caturla et al., Lithiated (E)-5-tosyl-4-pentenoic acid: A new delta-acyldienyl anion equivalent, TETRAHEDR L, 40(32), 1999, pp. 5957-5960
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
32
Year of publication
1999
Pages
5957 - 5960
Database
ISI
SICI code
0040-4039(19990806)40:32<5957:L(AAND>2.0.ZU;2-W
Abstract
(E)-5-Tosyl-4-pentenoic acid (9), prepared from 4-pentenoic acid by stereos elective in situ iodosulfonylation-dehydroiodination, is lithiated at vinyl ic position and reacts with carbonyl compounds affording stereoselectively 6-hydroxy acids 12. These acids have been stereoselectively transformed int o methyl (2E,4E)-6-hydroxydienoates 13, by esterification with trimethylsil yldiazomethane followed by delta-dehydrosulfinylation with DBU, or into (Z) -gamma-lactones 14 by heating in the presence of p-toluenesulfonic acid. (C ) 1999 Elsevier Science Ltd. All rights reserved.