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Paper | Regular issue | Vol 78, No. 5, 2009, pp.1223-1233
Published online, 29th December, 2008
DOI: 10.3987/COM-08-11610
Synthesis and Retro Aza Diels-Alder Reaction of Some New Isoquinuclidine Derivatives

Liliana Marzorati,* Patrícia Busko Di Vitta, Blanka Wladislaw, Julio Zukerman Schpector, and Claudio Di Vitta*

*Chemistry Institute of the University of São Paulo, Av. Prof. Lineu Prestes 748, 05508-000, São Paulo, Brazil

Abstract

N-Benzyl- and N-(α-methoxycarbonylethyl)-2,4,6-triphenyl-1,2-dihydropyridines were submitted to Diels-Alder reactions with maleic anhydride or N-phenylmaleimide yielding, diastereoselectively, the corresponding endo-anti adducts. These novel isoquinuclidines showed to be resistant to N-alkylation or N-protonation, undergoing an unexpected fragmentation via a retro aza Diels-Alder process.