REACTIVITY OF 2-CYANO-1,4,5,6-TETRAHYDRO-1-PYRIDINECARBOXYLIC ACID-ESTERS TOWARDS VARIOUS NUCLEOPHILES - REGIOSELECTIVITY AND STEREOSELECTIVITY OF THE ATTACK

The synthesis and reactivity of the title compounds towards nucleophil es are discussed. The regio-and diastereoselectivity of the attack is highly dependent on the carbamic ester and the type of nucleophile app lied. Both Michael type addition across the activated double bond and S(N)2T reaction at the carbamate carbon atom were observed. Structure assignment of the adducts in solution and in the solid state was perfo rmed utilizing high temperature NMR techniques as well as single cryst al X-ray diffraction.