Standard Article

α-Amidoalkylations at Carbon

  1. Harold E. Zaugg1,†,
  2. William B. Martin2,†

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or014.02

Organic Reactions

Organic Reactions

How to Cite

Zaugg, H. E. and Martin, W. B. 2011. α-Amidoalkylations at Carbon. Organic Reactions. 14:2:52–269.

Author Information

  1. 1

    Abbott Laboratories

  2. 2

    Lake Forest College

Publication History

  1. Published Online: 15 MAR 2011


This chapter is concerned with reactions that lead to the formation of a new carbon-carbon bond by the replacement of X (eg, halogen, -OH, -OR, -OCOR, -NHCOR -NR 2 or NR3) from an electrophilic reagent, RCON(R')CH(R”)X. The R' group may be hydrogen or alkyl or an acyl group. In a few cases a sulfonyl group may replace the acyl group of the electrophilic reagent. The nucleophiles that react with these reagents fall into two broad groups: aromatic compounds and aliphatic compounds containing reactive methylene or methane groups. Methods for preparing the electrophilic reagents are included in this chapter.


  • alpha-amidoalkylations;
  • carbon;
  • electrophiles;
  • nucleophiles;
  • aromatic carbon atoms;
  • aliphatic carbon atoms;
  • electrophilic reagents;
  • preparation;
  • structures;
  • experimental conditions