Birch Reduction
Reductive Alkylation of Enones
Mild oxidation method used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones.
Birch-type reductive alkylation, named after Arthur Birch, uses alkali metals (Na or Li) in liquid ammonia to produce a reducing agent that typically acts alongside a proton source (usually alcohol) to selectively reduce enones to lithium enolates.1 2 3 4 5 These enolates can undergo regioselective C-alkylation with alkyl halides, enabling controlled functionalization of unsymmetrical ketones. 1 2 3 4 5