Enamine synthesis

Enamine review A. G. Cook, Ed., Enamines Synthesis, Structure and Reactions, 2d ed., M. Dekker, New York, 1988. 

A. Gilbert Cook, Enamines Synthesis, Suucture and Reactions, p. 115. Marcel Dekker, London, 1969. 

When the nitrogen of the substrate contains a chiral R group, both the Stork enamine synthesis and the enamine salt method can be used to perform enantio-selective syntheses. " ... 

Although not formally the enamine synthesis, reaction of an enamine with methyl hromoacetate in the presence of indium metal leads to a-aUcylation R2N-CH=CHR R2N-CH(R )CHR. ... 

ENDOCYCLIC ENAMINE SYNTHESIS JV-METHYL- 2- PHENYL- A -TETRA-HYDROPYRIDINE, 54, 93 Enol acetates, acylation of,... 

ENDOCYCLIC ENAMINE SYNTHESIS N-METHYL-2-PHENYL-A2-TETRAHYDROPYRIDINE... 

Stork enamine synthesis takes advantage of the fact that an aldehyde or ketone reacts with a secondciry cimine to produce an enamine. Enamines cire resonance stabilized (see Figure 15-25) and have multiple applications. In the first resonance structure, the nitrogen is the nucleophile, while in the second resonance structure, the Ccirbanion is the nucleophile. Some commonly used secondary amines, pyrrolidine, piperidine, and morpholine, are shown in Figure 15-26. 

Some secondary amines commonly used in the Stork enamine synthesis. 

Stork Enamine Synthesis A reaction leading to the formation of an a-alkyl or a-carbonyl compound from an alkyl or aryl halide reacting with an enamine. 

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