Strecker Amino Acid Synthesis

A. Strecker, Ann. 75, 27 (1850); 91, 349 (1854).

Synthesis of α-amino acids by reaction of aldehydes with ammonia and hydrogen cyanide followed by hydrolysis of the resulting α-aminonitriles. Safer, milder, and more selective reaction conditions have been developed, especially in regard to asymmetric synthesis. The scope of the reaction has been extended to include primary and secondary amines:



Reviews: J. P. Greenstein, M. Winitz, Chemistry of the Amino Acids vol. 3 (New York, 1961) pp 698-700; G. C. Barrett, Chemistry and Biochemistry of the Amino Acids (Chapman and Hall, New York, 1985) pp 251, 261. Asymmetric synthesis using enantiopure sulfinimines: F. A. Davis et al., Tetrahedron Letters 35, 9351 (1994); idem et al., J. Org. Chem. 61, 440 (1996). Asymmetric syntheses: M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 120, 4901 (1998); E. J. Corey, M. J. Grogan, Organic Letters 1, 157 (1999). Review of stereoselective synthesis: R. O. Duthaler, Tetrahedron 50, 1539-1650 (1994); T. K. Chakraborty et al., ibid. 51, 9179-9190 (1995). Cf. Bucherer-Bergs Reaction.