Concept explainers
Synthetic Applications of Enamines
The formation of enamines by the reaction of
described in Section
When preparing enamines, the reaction is normally carried out by heating in benzene as the solvent. No catalyst is necessary, but
Enamines resemble enols in that electron-pair donation makes their double bond electron-rich
and nucleophilic.
Because nitrogen is a better electron-pair donor than oxygen, an enamine is more nucleophilic thanan enol. Enamines, being neutral molecules, are, however, less nucleophilic than enolates, which areanions.
Reactions of enamines with electrophiles
Pyrrolidine is the secondary amine used most often for making enamines from aldehydes and
ketones.
For synthetic purposes, the electrophilic reagents that give the best yields of
Acyl chlorides and acid anhydrides.
Michael acceptors:
pyrrolidine derivative. Of the following, which one is the best pyrrolidine derivative to use
in this enantioselective synthesis?
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