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Paper | Regular issue | Vol 31, No. 7, 1990, pp.1251-1260
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5319
New Synthetic Approach to 1-Azabicyclo[x.y.0]alkalne Skeletons from β-Enamino Diesters Derived from Meldrum’s Acid

Mansour Haddad, Jean Pierre Célérier, Gjergj Haviari, Gérard Lhommet,* Hamid Dhimane, Jean Claude Pommelet, and Josselin Chuche

*Laboratoire de Chimie des Hétérocycles URA 455, Université P. et M. Curie, 4, Place Jussieu - case 43 F-75252 Paris Cedex 05, France

Abstract

Two complementary methods for the synthesis of title compounds (4 and 6), namely, monodecarboxylating transesterification of β-enamino esters 2 followed by intramolecular cyclization of 3, and direct cyclization of 2 under flash vaccum thermolysis conditions, have been elaborated. Further investigations allowed the identification of β-enamino acid chloride 5 as a stable intermediate in the direct cyclization of 2 into 6. Azabicyclic compounds 4 were stereospecifically converted to bicyclic β-amino alcohols 9 by means of stereocontrolled carbon-carbon double bond catalytic hydrogenation followed by ester moiety reduction.