Question

Advantages of enamine approach over enolate approach

Answer 1

The most important advantages are:

Enamines are neutral, but enolates are deprotonated, making enamines less prone to over-reaction (i.e. adding more than one alkyl group by accident). We like more control over our reactants.

Enamines are experimentally easier to prepare since with enolates, you have to force an irreversible reaction using something like lithiumdiisopropyl amide (LDA), but with enamines you don't. (If you use  

OH

−

on a carbonyl compound, the equilibrium is not heavily skewed towards the enolate.)