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Synthesis 1970; 1970(2): 49-73
DOI: 10.1055/s-1970-21579
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Recent Synthetic Methods Involving Intermolecular alpha;-Amidoalkylation at Carbon

Harold E. ZAUGG*
  • *Abbott Laboratories, North Chicago, Illinois 60064, USA.
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Publication History

Publication Date:
12 September 2002 (online)

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This paper summarizes the work that has been done in the field since the most recent review of the subject1, i. e. literature coverage from January, 1963 to June, 1969. Briefly, the scope includes any reaction resulting in the attachment of an α-amidoalkyl group to a carbon atom of another molecule. The electrophilic amidoalkylation reagents generally can be represented by the structure, R-CO-N(R′)-CH(R″)-X, where X, the leaving group, is -OH, -OR, -O-CO-R, -NH-CO-R, -NR2, -NR3 +, or halogen (in the tables this order will be used in listing the reagents). The group R′ may be hydrogen, alkyl, or a second acyl group. When R′ is hydrogen, HX may be eliminated in certain cases to give the corresponding acylimine, R-CO-N = CH-R″, also an effective α-amidoalkylating agent. Compounds bearing carbon atoms sufficiently nucleophilic to be susceptible to attack by the amidoalkylation agents represent a wide variety of structural types. They include aromatic compounds, olefins, acetylenes, ketenes, carbenoid compounds, and carbanionoid compounds derived from active methylenes, Grignard reagents, and other organometallics. The review surveys α-amidoalkylation of 1. Aromatic Compounds 2. Mono-olefins 3. Conjugated Dienes 4. Acetylenes 5. Ketenes 6. Carbenoid Carbon 7. Active Methylene Compounds (and HCN) 8. Grignard Reagents

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