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Strecker Synthesis: History
Please note this is an old version of this entry, which may differ significantly from the current revision.
Subjects: Chemistry, Organic
Contributor: Helena Kang

The Strecker synthesis is a multicomponent route to α-amino acids through formation and subsequent hydrolysis of an α-aminonitrile. An aldehyde or ketone first condenses with ammonia or an amine to form an imine or iminium species; cyanide then adds to the imine carbon, generating an α-aminonitrile whose nitrile group is hydrolyzed to a carboxylic acid [1]. The carbonyl carbon becomes the α-carbon of the amino-acid product, while the nitrogen and cyanide supply the amino and carboxyl-derived functionalities, respectively. When a prochiral imine is attacked in an achiral environment, a racemic product normally results. Catalytic asymmetric Strecker variants use chiral catalysts to discriminate the two imine faces and furnish enantioenriched α-aminonitriles [2]. The reaction is distinguished from direct reductive amination because cyanide forms a new carbon–carbon bond and the nitrile, rather than a reducing agent, is the immediate precursor of the carboxyl group.

  • Strecker synthesis
  • α-aminonitrile
  • amino acid
  • imine cyanation

Organic Chemistry Synthesis Methods • Organic Chemistry • Chemistry • Physical Sciences

References

  1. Wang, Z. Strecker Synthesis; Wiley: Hoboken, NJ, United States, 2010; pp. 2710-2717. [CrossRef]
  2. Jun Wang; Xiaohua Liu; Xiaoming Feng; Asymmetric Strecker Reactions. Chem. Rev. 2011, 111, 6947-6983, 10.1021/cr200057t.
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