DABAL-Me3: A versatile methylating agent

Abstract

(A) Woodward and co-workers reported the first assymmeytric synthesis of secondary alchohols from prochiral aldehydes in the presence of nickel(acetylacetone)2 and a phosphoroamidite ligand.3 (Chemical Equation Presented) (B) Methylation of aryl and vinyl halides is another example of a very efficient route of forming C-C bonds. DABAL-Me 3 is quite capable of carrying out this transformation.4 (Chemical Equation Presented) (C) In pursuance of developing a suitable route for addition of an alkyl group to different Michael acceptors, Woodward and co-workers used DABAL-Me3 in an enantioselective manner employing appropriate ligands.5 (Chemical Equation Presented) (D) Direct formation of amides from the corresponding inactivated esters and lactones can be conveniently carried out with DABAL-Me3 excluding the risk of using other pyrophoric AlR3 reagents.6 Woodward and co-workers later utilized microwave irradiation in DABAL-Me3-mediated amide bond formation in order to carry out the reaction in a shorter span of time.7 (Chemical Equation Presented) © Georg Thieme Verlag Stuttgart.