An overview is provided of the utilitarian role that allylindation
under aqueous conditions can play in a variety of synthetic contexts.
These include the diastereoselective allylation of chiral aldehydes,
the consequences of coupling geometrically biased allylic bromides,
the realization of 1,4-asymmetric induction, and an analysis of
competitive intramolecular/intermolecular chelation options.
Also presented are the results of diastereoselective additions to α-oxygenated
ketones and to 2,3-azetidinediones. Synthetic applications include
a practical alternative to the Knoevenagel reaction of
aliphatic aldehydes, the formation of α-methylene-γ-lactones
fused to medium and large rings, and the intercalation of multiple
carbon atoms between the carbonyls of α-diketones.
allylations - water as solvent - chelation
control - 1,4-asymmetric induction - 2,3-azetidinediones
