HORNER-WADSWORTH-EMMONS OLEFINATION OF NONSTABILIZED PHOSPHONATES - ANEW SYNTHETIC APPROACH TO BETA,GAMMA-UNSATURATED AMIDES

Authors
JANECKI T BODALSKI R WIECZOREK M BUJACZ G
Citation
T. Janecki et al., HORNER-WADSWORTH-EMMONS OLEFINATION OF NONSTABILIZED PHOSPHONATES - ANEW SYNTHETIC APPROACH TO BETA,GAMMA-UNSATURATED AMIDES, Tetrahedron, 51(6), 1995, pp. 1721-1740
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
6
Year of publication
1995
Pages
1721 - 1740
Database
ISI
SICI code
0040-4020(1995)51:6<1721:HOONP->2.0.ZU;2-D
Abstract
Aminolysis of readily accessible beta-diethoxyphosphonyl-gamma-butyrol actones 5 and 22 provides a convenient entry to (E)-beta,gamma-unsatur ated amides 8 and 24 respectively. The key step of the aminolysis invo lves elimination of diethoxyphosphoric acid from the corresponding bet a-hydroxyalkylphosphonates 7 and 23. Stereochemistry of the amides 8 a nd 24 results from their consecutive base catalyzed isomerization.