The C=N double bond of certain cis- or trans-cycloalkane and diexo- or diendo-norbornane-condensed pyridazinones was reduced with NaBH3CN. The cis- or trans nature of the starting cycloalkane derivatives was always retained in the saturated products, with a high degree of diastereoselectivity: the hydrogen on the new stereocenter and the annelational hydrogen next to the carbonyl always exhibited the same steric orientation. The stereostructures were determined by means of nmr measurements and confirmed by molecular modelling.
ASJC Scopus subject areas
- Organic Chemistry