A study of the diels-alder reaction of 3-oxabicyclo[3.3.0]oct-1(5)-ene-2,4-dione with cyclopentadiene and some related dienes

P. Camps, J. Castañé, M. Feliz, M. Figueredo

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Abstract

The reaction of 3-oxabicyclo[3.3.0]oct-l(5)ene-2,4-dione, 2, with cyclopentadiene, 3, 5,5-diethoxycyclopentadiene, 4, and 6,6-dimethylfulvene, 5, is studied. Reaction of 2 and 3 yields the expected endo-adduct, while reaction of 2 and 5 gives a mixture of the endo- and exo-adducts whose ratio is slightly dependent on the reaction conditions. Attractive electrostatic interactions in the transition state leading to the exo-adduct can explain the absence of endo stereoselectivity in the last reaction. Steric factors seem to be responsible for the absence of reaction between 2 and 4. The analysis of the 13C NMR spectra of these adducts and some derived compounds confirms the tentative configuration assignment carried out on the basis of PMR data. Also, the synthesis of dimethyl(1R,2S,6R,7S)-10-oxotricy-clo [5.2.1.02.6]decane2,6-decarboxylate, 1, from the endo-adduct of the reaction of 2 and 5, is described. © 1984.
Original languageEnglish
Pages (from-to)5235-5242
JournalTetrahedron
Volume40
Issue number24
DOIs
Publication statusPublished - 1 Jan 1984

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