DIASTEREOFACIAL SELECTIVITY OF THE CYCLOADDITION OF DIAZO-COMPOUNDS TO ENONES

Authors
GALLEY G PATZEL M JONES PG
Citation
G. Galley et al., DIASTEREOFACIAL SELECTIVITY OF THE CYCLOADDITION OF DIAZO-COMPOUNDS TO ENONES, Tetrahedron, 51(6), 1995, pp. 1631-1640
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
6
Year of publication
1995
Pages
1631 - 1640
Database
ISI
SICI code
0040-4020(1995)51:6<1631:DSOTCO>2.0.ZU;2-Y
Abstract
Chiral alpha,beta-unsaturated gamma-allroxy- or gamma-amino-ketones (e nones) 1 react with diazo compounds in a stereoselective manner afford ing conjugated Delta(2)-pyrazolines 5 and 6. In all cases syn-selectiv ity for the cycloaddition was observed. The diastereomeric ratio is im proved at lower temperatures, but no significant influence of high pre ssure is observed. Carrying out this reaction with (E) and (Z) derivat ives of the same enone 1 leads to identical products.