IMETHYL-1,3-DIOXOLAN-4-YLMETHYLEN]-5(4H)-OXAZOLONE AS THE DIENOPHILE IN ASYMMETRIC DIELS-ALDER REACTIONS .2.

Authors
BUNUEL E CATIVIELA C DIAZDEVILLEGAS MD
Citation
E. Bunuel et al., IMETHYL-1,3-DIOXOLAN-4-YLMETHYLEN]-5(4H)-OXAZOLONE AS THE DIENOPHILE IN ASYMMETRIC DIELS-ALDER REACTIONS .2., Tetrahedron : asymmetry, 7(5), 1996, pp. 1431-1436
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
5
Year of publication
1996
Pages
1431 - 1436
Database
ISI
SICI code
0957-4166(1996)7:5<1431:IATDI>2.0.ZU;2-5
Abstract
Diels-Alder reaction of Z-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan -4 -ylmethylen]-5(4H)-oxazolone and Danishefsky's diene is studied. Therm ally induced reaction took place at room temperature with a high diast ereofacial selectivity and Diels-Alder adducts, obtained in very high diastereomeric purity, were easily transformed into valuable compounds . The stereochemistry of the adducts has been elucidated by single cry stal X-ray structure determinations, H-1-NMR analysis and mechanistic considerations. Copyright (C) 1996 Elsevier Science Ltd