Collect. Czech. Chem. Commun. 1979, 44, 2653-2659

Synthesis and chiroptical properties of (-)-(1R)-3-azatricyclo[5,4,0,04,9]undecan-2-one - A lactam with non-planar cis-amide group

Miloš Tichý, Petr Maloň, Ivo Frič and Karel Bláha

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


The title compound (-)-II was prepared starting from (-)-(2S)-endo-bicyclo[2,2,2]oct-5-ene-2-carboxylic acid ((-)-III). Parameters of the dichroic bands obtained in solvents of various polarity indicate the presence of a non-planar amide group in (-)-II. This amide group is of an opposite chirality and deviates less from planarity than the amide group in (-)-(3S)-4-azatricyclo[4,4,0,03,8]decan-5-one (I). Comparison of the calculated ORD curves with the experimental ones shows that molecular chirality of the σ-skeleton does not participate directly in the dichroic absorption of the amide group.