A. Fisher, E. Oppenheimer, Sasson Cohen
1975
Citations
0
Influential Citations
5
Citations
Journal
Tetrahedron
Abstract
Abstract Michael addition of ethyl malonate, alkylmalonate and phenylacetate to 2-methylene-quinuclidin-3-one, followed by NaBH 4 reduction of the 3-oxo group in the resulting adduct, then acid hydrolysis and decarboxylation (in the case of malonates) gave 6-oxa-1-azatricyclo-(4.2.2.0 2,7 )dodecan-5-one, its 4-alkyl and 4-aryl derivatives. A minor byproduct is 2-( trans -3-hydroxyquinuclidin-2-yl)-α-alkyl-propanoic acid which is unable to undergo cyclization to δ-lactone.