59995-83-4Relevant academic research and scientific papers
Dioxopyrrolines. XXXVI. Photocycloaddition Reaction of 4-Ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione to Acyclic Olefins. Structural and Stereochemical Assigment of the Photocycloadducts
Sano, Takehiro,Horiguchi, Yoshie,Tsuda, Yoshisuke,Furuhata, Kimio,Takayanagi, Hiroaki,Ogura, Haruo
, p. 9 - 22 (2007/10/02)
The photocycloaddition of the dioxopyrroline 1 to olefins with electron donating substituents proceeded with regio- and stereo-selectivity to give the 7-substituted 2-azabicycloheptane-3,4-diones 2 and 3, together with, in a few instances, the dihydropyridone 4.The stereochemistries of the adducts were dependent on the nature of the olefins.Olefins carrying phenyl, vinyl, and alkyl substituents afforded the exo-adducts 2, while olefins carrying an O-substituent afforded the endo-adducts 3, predominantly.The structures of these cycloadducts were established by X-ray crystallographic analyses, chemical correlations, and spectroscopic means.Keywords-photocycloaddition; 1H-pyrrole-2,3-dione; dioxopyrroline; 2-azabicyclo-heptane-3,4-dione; electron rich olefin; stereochemistry; cycloadduct; X-ray analysis
