Effect of amines on the selective bromination of some beta-substituted-2-butenoic esters

Authors
Nakada, M Kojima, E Ichinose, H
Citation
M. Nakada et al., Effect of amines on the selective bromination of some beta-substituted-2-butenoic esters, SYN COMMUN, 30(5), 2000, pp. 863-868
Citations number
7
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
30
Issue
5
Year of publication
2000
Pages
863 - 868
Database
ISI
SICI code
0039-7911(2000)30:5<863:EOAOTS>2.0.ZU;2-8
Abstract
The effect of amines on the selective bromination of some beta-substituted- 2-butenoic esters is described. The bromination of methyl (Z)-4-t-butyldiph enylsilyloxy-3-methylbutenoate 2 in the presence of DIPEA (N,N-diisopropyle thylamine) and the:successive treatment of the obtained dibromide with pota ssium t-butoxide afford the desired Z bromide selectively. But the correspo nding E bromide forms exclusively when 2, 6-di-t-butyl-4-methylpyridine is used in the bromination.