Synthesis and cycloaddition reactions of ethyl 3-aryl-2-(perfluoroalkanesulfonyl)propenoates - A revised stereochemistry of the cyclopentadiene adducts

Authors
Goumont, R Magder, K Tordeux, M Marrot, J Terrier, F Wakselman, C
Citation
R. Goumont et al., Synthesis and cycloaddition reactions of ethyl 3-aryl-2-(perfluoroalkanesulfonyl)propenoates - A revised stereochemistry of the cyclopentadiene adducts, EUR J ORG C, (11), 1999, pp. 2969-2976
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
11
Year of publication
1999
Pages
2969 - 2976
Database
ISI
SICI code
1434-193X(199911):11<2969:SACROE>2.0.ZU;2-K
Abstract
Ethyl 3-aryl-2-(perfluoroalkanesulfonyl)propenoates were prepared by the Kn oevenagel reaction from various aldehydes and ethyl (trifluoromethanesulfon yl)acetate or ethyl (nonafluorobutanesulfonyl)acetate. These deactivated ol efins were used in Diels-Alder cycloaddition reactions with cyclopentadiene . The reactions occurred at room temperature to give [4+2] cycloadducts as racemates. The endo stereochemistry of the carboxylic ester and aryl groups was unambiguously assigned by NOE experiments and X-ray analysis.