[leelee]

My notes:
Enolates can be made using NaOH, and they are a better nucleophile than enamines. However, the OH- is a better nucleophile than enolate and so it will react first. So, enamines are better in this case because they are acid catalyzed.

this has me confused...is this always the case? How would halogenation or alkyation be able to occur then?

thanks.

[GSR]

Hi,

Enolates are more nucleophilic than enamines, because enolate has formal negative charge and electronegativity of N is less than O. Enolates accept most electrophiles at carbon so very useful to make new carbon-carbon bonds.

GSR

[movies]

Metalloenamine (like an enolate, but with nitrogen), however, are better nucleophiles than enolates.  They are quite a bit more reactive and can add to less reactive electrophiles such as epoxides, which enolates will generally not react with epoxides.