DIASTEREOFACIAL SELECTIVITY IN THE DIELS-ALDER REACTION OF 5(S)-E-5,6-O-ISOPROPYLIDEN-HEX-3-EN-2-ONE WITH CYCLOPENTADIENE

Authors
GALLEY G MUGGE C JONES PG PATZEL M
Citation
G. Galley et al., DIASTEREOFACIAL SELECTIVITY IN THE DIELS-ALDER REACTION OF 5(S)-E-5,6-O-ISOPROPYLIDEN-HEX-3-EN-2-ONE WITH CYCLOPENTADIENE, Tetrahedron : asymmetry, 6(9), 1995, pp. 2313-2318
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
9
Year of publication
1995
Pages
2313 - 2318
Database
ISI
SICI code
0957-4166(1995)6:9<2313:DSITDR>2.0.ZU;2-7
Abstract
The effect of temperature, catalyst and pressure on the outcome of the Diels-Alder reaction of 5(S)-E-5, 6-O-isopropyliden-hex-3-en-2-one wi th cyclopentadiene was investigated. All four possible Diets-Alder add ucts were isolated and characterized on the basis of single crystal X- ray analysis and NMR experiments. Et(2)AlCl was found to be the most e ffective catalyst to give exclusively the endo-isomers.