Enamine acylation

Reaction with an acid chloride

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In the above mechanism, the attack of the enamine and the expulsion of the chlorine have been shown as two separate steps. This has been done to coincide with conventional teaching. However this reaction may only occur in one step: as the enamine attacks, the chlorine leaves at the same time (as shown in the transition state).

G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz and R. Terrell, J. Am. Chem. Soc., 1963, 85, 207–222.