A SULFINYL TRIALKOXYCARBONYL ETHENE AS A NEW ENANTIOPURE DIENOPHILE IN ASYMMETRIC DIELS-ALDER REACTIONS

Authors
CARRETERO JC RUANO JLG CABREJAS LMM
Citation
Jc. Carretero et al., A SULFINYL TRIALKOXYCARBONYL ETHENE AS A NEW ENANTIOPURE DIENOPHILE IN ASYMMETRIC DIELS-ALDER REACTIONS, Tetrahedron, 51(30), 1995, pp. 8323-8332
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
30
Year of publication
1995
Pages
8323 - 8332
Database
ISI
SICI code
0040-4020(1995)51:30<8323:ASTEAA>2.0.ZU;2-P
Abstract
The synthesis and the asymmetric Diels-Alder reactions of the enantiom erically pure (S)-p-tolylsulfinyl trialkoxycarbonyl ethene 3 with cycl ic and acyclic dienes are reported. pi-Facial selectivity and regiosel ectivity are very high in all studied cases. Reactions with cyclopenta diene exhibit moderated or high exo-selectivity, which disappears with acyclic dienes. The use of high pressure improves the pi-facial selec tivity but does not substantially modify the endo-exo selectivity.