Unusual Stereoselectivity in the Diels-Alder Addition of Cyclpentadiene with the Bicyclooctene Nucleus

Article abstract of DOI:10.1021/jo00076a039

Cyclopentadiene adds to the substituted and electronically activated double bond of bicyclo<2.2.2>octa-2,5-diene-2,3-dicarboxylic anhydride with pronounced endo selectivity.Only two of the four possible stereoisomers were formed.The stereochemical course of the reaction was determined by X-ray crystallography and by a combination of chemical and sppectroscopic techniques.