Tetrahedron

β-Enaminoesters bicycliques: Synthese et reduction stereospecifiques. Acces a l'isoretronecanol, la trachelanthamidine, la lupinine et l'epilupinine

JP Célérier, M Haddad, C Saliou, G Lhommet…

Index: Celerier, J. P.; Haddad, M.; Saliou, C.; Lhommet, G. Tetrahedron, 1989 , vol. 45, # 19 p. 6161 - 6170

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Citation Number: 21

Abstract

The functionalized N-alkyl-β-enaminoesters 11 are precursors of nitrogen-bridged bicyclic β- enaminoesters 7. The compounds 7 are prepared either by intramolecular alkylation of β- enaminoesters 11 or by thermolysis of β-enaminoesters 6. A stereospecific reduction of compounds 7 under thermal control leads to bicyclic β-aminoesters 13, 14, 15 or 16 which are good precursors of natural aminoalcohols like lupinine 4 or isoretronecanol 2.