Structure Dependent Nickel Catalysed Transposition of N Allylamides to E or Z Enamides
The nickel catalysed transposition of a carbon carbon double bond of N allyl and N homoallyl amides is described. While the transposition of acyclic amides gave very high Z selectivity of the enamides, corresponding cyclic N allyl amides led exclusively to the E configured products. Thereby, we realised a stereodivergent approach to enamides that is dependent on the structure of the amide substituents. When homoallylic substrates are used, a temperature controlled single transposition to a Z allylic amide derivative at low temperature or a double transposition to an E enamide at elevated temperature could be achieved.