Reformatskii reaction

The Reformatskii reaction (often spelled Reformatsky reaction) is an organic reaction which condenses aldehydes 1 (or ketones) with α-halo esters 2 with metallic zinc to form β-hydroxy-esters 3. It was discovered by Sergei Nikolaevich Reformatskii.



The organozinc reagent, also called a 'Reformatskii enolate', is prepared by treating an alpha-halo ester with zinc dust. Reformatskii enolates are less reactive than Grignard reagents and hence nucleophillic addition to the ester group does not occur.

Some reviews have been published.

Variations
In one variation of the Reformatsky reaction an iodolactone is coupled with an aldehyde with triethylborane in toluene at -78°C.