DIASTEREOSELECTIVE HETERO-DIELS-ALDER CYCLOADDITION OF A C-NITROSO COMPOUND PREPARED STARTING FROM A HOMOCHIRAL IMIDAZOLIDIN-2-ONE

Authors
CARDILLO B GALEAZZI R MOBBILI G ORENA M ROSSETTI M
Citation
B. Cardillo et al., DIASTEREOSELECTIVE HETERO-DIELS-ALDER CYCLOADDITION OF A C-NITROSO COMPOUND PREPARED STARTING FROM A HOMOCHIRAL IMIDAZOLIDIN-2-ONE, Tetrahedron : asymmetry, 5(8), 1994, pp. 1535-1540
Citations number
41
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
8
Year of publication
1994
Pages
1535 - 1540
Database
ISI
SICI code
0957-4166(1994)5:8<1535:DHCOAC>2.0.ZU;2-0
Abstract
By Swern oxidation of the hydroxamic acid 3, prepared from the homochi ral imidazolidin-2-one 1, the transient C-nitroso derivative 4 is obta ined, and its cycloaddition to either cyclohexadiene or cyclopentadien e proceeds with high diastereoselection, owing to the conformational s tability of 4. The stereochemical outcome of the reaction is determine d from H-1 NMR data and further confirmed by the specific rotation val ue of 7, obtained by cleavage of the major cycloadduct 5a.