EFFICIENT SYNTHESIS OF 4-ETHENYLIDENE-2-OXAZOLIDINONES VIA PALLADIUM-CATALYZED AMINOCYCLIZATION OF 2-BUTYN-1,4-DIOL BISCARBAMATES

Authors
KIMURA M WAKAMIYA Y HORINO Y TAMARU Y
Citation
M. Kimura et al., EFFICIENT SYNTHESIS OF 4-ETHENYLIDENE-2-OXAZOLIDINONES VIA PALLADIUM-CATALYZED AMINOCYCLIZATION OF 2-BUTYN-1,4-DIOL BISCARBAMATES, Tetrahedron letters, 38(22), 1997, pp. 3963-3966
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
22
Year of publication
1997
Pages
3963 - 3966
Database
ISI
SICI code
0040-4039(1997)38:22<3963:ESO4VP>2.0.ZU;2-0
Abstract
4-Ethenylidene-2-oxazolidinones 2, 6, and 9 are prepared in reasonable yields by the reaction of 2-butyn-1,4-diol biscarbamates in the prese nce of catalytic amounts of Pd-2(dba)(3) . CHCl3 (0.005 equiv) ad trie thylamine (0.1 equiv). The allenic three carbons are not aligned strai ght, but considerably distorted (173.6 degrees); the enamine double bo nd is reactive toward unsaturated amides (providng 4) and methyl vinyl ketone (providing 10). (C) 1997 Elsevier Science Ltd.