An air-stable "methyl anion"

19 August 2005

The DABCO adduct of trimethyl aluminium, (Me_³Al)_².DABCO (also referred to as DABAL-Me_³) has been found to be air-stable. It is a free-flowing white powder which can be weighed out on the bench without the need for an inert atmosphere, and can be stored in standard glassware. Under nickel catalysis in the presence of a chiral ligand, this effectively adds “methyl anion” to aldehydes to give the corresponding chiral secondary alcohols in generally good enantiomeric excess.

* K. Biswas, O. Prieto, P.J. Goldsmith and S. Woodward, Angew. Chem. Int. Ed., 2005, 44, 2232-2234.