Regio- and diastereo-selectivity in 1,3-dipolar cycloadditions of nitrile oxides to 4-substituted cyclopent-2-enones

Authors
Adembri, G Giorgi, G Lampariello, RL Paoli, ML Sega, A
Citation
G. Adembri et al., Regio- and diastereo-selectivity in 1,3-dipolar cycloadditions of nitrile oxides to 4-substituted cyclopent-2-enones, J CHEM S P1, (16), 2000, pp. 2649-2656
Citations number
44
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14704358 → ACNP
Issue
16
Year of publication
2000
Pages
2649 - 2656
Database
ISI
SICI code
1470-4358(2000):16<2649:RADI1C>2.0.ZU;2-C
Abstract
The behaviour of 4-hydroxy-4-methylcyclopent-2-enone and related 4-substitu ted cyclopent-2-enones towards 1,3-dipolar cycloaddition with nitrile oxide s is studied. The reactions are always completely regioselective while the diastereofacial selectivity depends on the nature of the substituents. Rema rkably, the reaction of 4-acetoxycyclopent-2-enone shows complete regio- an d diastereo-facial selectivity.