Lithium trimethylalkynylaluminate, a new chemoselective alkynylating agent

Lithium trimethylalkynylaluminates, prepared conveniently by reacting trimethylaluminum with lithium alkynide, readily react with aldehydes and ketones to give the corresponding propargyl alcohols in 70-95% yields. The reaction is highly chemoselective; thus many other functional groups such as amides, nitriles, epoxides and halogen compounds are inert under the reaction conditions. The reagents also show an excellent 1,2-regiospecificity in the reactions with cyclic or acyclic α,β-unsaturated carbonyl compounds.