INTRAMOLECULAR DIELS-ALDER REACTIONS OF VINYLSULFONAMIDES

Authors
METZ P SENG D FROHLICH R WIBBELING B
Citation
P. Metz et al., INTRAMOLECULAR DIELS-ALDER REACTIONS OF VINYLSULFONAMIDES, Synlett, (8), 1996, pp. 741
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
8
Year of publication
1996
Database
ISI
SICI code
0936-5214(1996):8<741:IDROV>2.0.ZU;2-L
Abstract
The vinylsulfonamides 3 of the furan-containing N-benzylamines 2 cycli ze at room temperature to give the delta-sultams 4 with high diastereo selectivity. For the vinylsulfonamides 6 featuring a three atom tether connecting the furan and the dienophile moieties, the equilibrium bet ween 6 and the gamma-sultam 7 is largely shifted towards 7 for N-benzy l substituted 6c in refluxing toluene.