4-SUBSTITUTED PROTOANEMONIN IN INTRAMOLECULAR CYCLOADDITION REACTIONSOF NONSTABILIZED AZOMETHINE YLIDES

Authors
GRIGG R SAVIC V THORNTONPETT M
Citation
R. Grigg et al., 4-SUBSTITUTED PROTOANEMONIN IN INTRAMOLECULAR CYCLOADDITION REACTIONSOF NONSTABILIZED AZOMETHINE YLIDES, Tetrahedron, 53(30), 1997, pp. 10633-10642
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
30
Year of publication
1997
Pages
10633 - 10642
Database
ISI
SICI code
0040-4020(1997)53:30<10633:4PIICR>2.0.ZU;2-B
Abstract
The intramolecular cycloaddition reactions of non-stabilised azomethin e ylides generated by condensation of 4-(3-propanalyl)-5-methylene-2(5 H)furano and cyclic amino acids were investigated. The reactions proce eded via highly stereoselective formation of anti-dipoles followed by cycloaddition reactions on either the alpha,beta- or gamma,delta- doub le bond to produce polycyclic cycloadducts in good yield. Both double bonds of the lactone moiety proved to be efficient dipolarophiles. (C) 1997 Elsevier Science Ltd.