TY - JOUR
T1 - Circular dichroism of heterocyclohexan-4-onic systems-II. The synthesis of the 8-azabicyclo [3,2,1] octanic system
AU - Kashman, Y.
AU - Cherkez, S.
PY - 1972
Y1 - 1972
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0009473897&partnerID=8YFLogxK
U2 - 10.1016/0040-4020(72)80064-4
DO - 10.1016/0040-4020(72)80064-4
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AN - SCOPUS:0009473897
SN - 0040-4020
VL - 28
SP - 155
EP - 165
JO - Tetrahedron
JF - Tetrahedron
IS - 1
ER -