PRACTICAL PALLADIUM-MEDIATED DEPROTECTIVE METHOD OF ALLYLOXYCARBONYL IN AQUEOUS-MEDIA

Citation
Jp. Genet et al., PRACTICAL PALLADIUM-MEDIATED DEPROTECTIVE METHOD OF ALLYLOXYCARBONYL IN AQUEOUS-MEDIA, Tetrahedron, 50(2), 1994, pp. 497-503
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
50
Issue
2
Year of publication
1994
Pages
497 - 503
Database
ISI
SICI code
0040-4020(1994)50:2<497:PPDMOA>2.0.ZU;2-2
Abstract
The Allyloxycarbonyl (Alloc) moiety can be removed smoothly and select ively in good yield (73-100%) from allylic eaters, carbamates and carb onates by aqueous Pd (0) catalyzed allyl transfer to diethylamine in a queous media employing a water soluble phosphine. The allyl scavenger as well as by product allyl diethylamine are volatile and easily remov ed in vacuo. In a two phase system an increased selectivity is seen. T he method has been successfully used for deprotection of a wide range of secondary amines or base sensitive derivatives and the catalyst is efficiently recycled.