Collect. Czech. Chem. Commun. 1984, 49, 834-839

(3R)-5-Azatricyclo[,8]decan-4-one, a lactam with a non-planar cis-amide group: Synthesis, geometry and chiroptical properties

Miloš Tichý, Ahmed M. Farag, Petr Maloň, Petr Kálal and Karel Bláha

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


Stereospecific synthesis of the title lactam (+)-I starting from (1R,5R,6R)-3-oxobicyclo[3.2.1]-octane-6-carboxylic acid is described. X-Ray structure determination has shown a marked non-planarityof the amide group in I. In accord with theoretical calculations, CD spectrum of the studied (+)-(3R)-enantiomer exhibits a positive n-π and negative π-π band. The rotational strength of the n-π transition is three times higher than that of the π-π transition, contrary to the behaviour of lactams with virtually planar amide groups.