Synthesis and Cycloaddition Reactions of Ethyl 3-Aryl-2-(perfluoroalkanesulfonyl)propenoates – A Revised Stereochemistry of the Cyclopentadiene Adducts

✍ Scribed by Régis Goumont; Karine Magder; Marc Tordeux; Jérome Marrot; François Terrier; Claude Wakselman

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 339 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199911)1999:11<2969::aid-ejoc2969>3.0.co;2-u

✦ Synopsis

Ethyl 3-aryl-2-(perfluoroalkanesulfonyl)propenoates were cyclopentadiene. The reactions occurred at room temperature to give [4+2] cycloadducts as racemates. The prepared by the Knoevenagel reaction from various aldehydes and ethyl (trifluoromethanesulfonyl)acetate or endo stereochemistry of the carboxylic ester and aryl groups was unambiguously assigned by NOE experiments and X-ethyl (nonafluorobutanesulfonyl)acetate. These deactivated olefins were used in Diels-Alder cycloaddition reactions with ray analysis.

purpose. The formation of a condensation product derived

The esters 4 were used in DielsϪAlder condensation resite ´de Versailles, actions with cylopentadiene (5). These reactions occurred