Circular dichroism of heterocyclohexan-4-onic systems-II. The synthesis of the 8-azabicyclo [3,2,1] octanic system

Y. Kashman, S. Cherkez

Research output: Contribution to journalArticlepeer-review

Abstract

The double Michael addition of amines to cyclohepta-2,6-dien-1-one was developed as a convenient and general method for the synthesis of new optically active N-substituted-nortropinones suitable for CD research (N-alkyl, N-aralkyl, N-cycloalkyl, N-carboalkoxyalkyl) as well as N-aryl-nortropinones; the structures proposed for the above compounds were confirmed by their NMR and mass spectra. The influence of the chiral N-substituent on the bicyclic skeleton protons, as seen in NMR, and its applications in conformational analysis are discussed. Eu(dpm)3 complexation was used for a more accurate interpretation of the NMR spectrum.

Original languageEnglish
Pages (from-to)155-165
Number of pages11
JournalTetrahedron
Volume28
Issue number1
DOIs
StatePublished - 1972

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