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Note | Special issue | Vol 70, No. 1, 2006, pp.619-626
Published online, 2nd November, 2006
DOI: 10.3987/COM-06-S(W)53
Synthesis of 4,7-Dihydro-2H-isoindole Derivatives via Diels-Alder Reaction of Tosylacetylene

Tetsuo Okujima,* Guangnan Jin, Yusuke Hashimoto, Hiroko Yamada, Hidemitsu Uno, and Noboru Ono*

*Department of Chemistry and Biology, Graduate School or Science and Engineering, Ehime University, Matsuyama 790-8577, Japan

Abstract

Diels-Alder reaction of ethynyl p-tolyl sulfone with 1,3-dienes gave the corresponding tosyl-1,4-cyclohexadienes. The resulting adducts could be converted into 4,7-dihydro-2H-isoindole derivatives including bicyclo[2.2.2]ocatadiene(BCOD)-fused pyrrole as an isoindole equivalent.