Enamine alkylation
= Enamine alkylation
<Enamine alkylation> forms a <carbon>–<carbon> <chemical bond> by using an <enamine> as a <carbon>-centred <nucleophile>. The nitrogen substituent donates <electron density> into the adjacent <carbon>–<carbon> double bond, enabling attack on an appropriate alkyl <electrophile>.
In the familiar carbonyl-functionalization sequence, a <ketone> or <aldehyde> first forms an <enamine> with an <amine>. <Carbon> alkylation gives an iminium-containing intermediate, and <hydrolysis> restores the <carbonyl group>. The net result can be substitution next to the original carbonyl <carbon>. Regioselectivity, competing nitrogen alkylation and substrate compatibility matter; the net product formula does not specify a universally selective reaction.