Palladium and copper-catalysed (C-C)-bond formation

Copper-Catalysed Conjugate Additions:
Conjugate 1,4-additions of carbon nucleophiles to α,β-unsaturated ketones are valuable C-C bond forming reactions that furthermore allow introduction of stereogenic centers.(1) Copper-catalysed reactions have been successfully employed in a variety of syntheses, for example for (-)-solavetivone(2) or prostaglandins.(3) Improvement of enantioselectivity through design of more effective ligands is thus highly desirable.
The ligands depicted below were synthesised and tested, with excellent enantioselectivities on selected substrates.
Muscone Synthesis:
Musk odorants are a family of molecules possessing a very nice smell, of central importance for the fragrance industry. Application of the methodology developed for the copper-catalysed conjugate addition to the synthesis of (S)-muscone allowed the obtaining of product 90 in high yield and excellent enantiomeric purity.
Multicomponent Heck-Allylic substitution Reaction:
Synthetic methodology which allows for a rapid increase in molecular complexity is extremely valuable in organic chemistry, particularly if it generates more than one new carbon-carbon bond at a time, accommodates considerable functionality and is broad in scope.
Design of a reaction sequence involving a Heck reaction followed by an allylic substitution allowed the obtaining of compound 141 depicted below.