Catalytic Enantioselective Allylation of Carbonyl Compounds and Imines

Various methodologies on the catalytic enantioselective addition of allylic nucleophiles to carbonyl compounds, imines, and imine derivatives, are discussed. Kobayashi described a highly enantioselective allylation of imines with substituted allylstannanes in the presence of a chiral zirconium catalyst derived from (R)-BINOL. The group of Loh extended the utility of the asymmetric allylation of aldehydes catalyzed by (S)-BINOL/InCl 3 complex through the use of ionic liquids as environmentally benign reaction medium. The first catalytic asymmetric allylation of imines was reported in 1998 by Y. Yamamoto and co-workers, who proposed that the bis-π-allylpalladium complex coordinates the imine, and the subsequent intramolecular allylation would proceed via a six-membered chair-like transition state. Cook et al. investigated the influence of different chiral ligands on the stereochemical outcome of the allylation of achiral hydrazone derived from benzaldehyde and N-amino oxazolidinone with equiv of allyliodide.