Strecker amino acid synthesis

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The Strecker amino acid synthesis is a series of chemical reactions that synthesize an amino acid from an aldehyde (or ketone).^[1][2] The aldehyde is condensed with ammonium chloride in the presence of potassium cyanide to form an α-aminonitrile, which is subsequently hydrolyzed to give the desired amino-acid.^[3][4]

While usage of ammonium salts gives unsubstituted amino acids, primary and secondary amines also successfully give substituted amino acids. Likewise, the usage of ketones, instead of aldehydes, gives α,α-disubtituted amino acids.^[5]

The traditional Strecker synthesis gives racemic α-amino nitriles, but recently several procedures utilizing asymmetric auxiliaries^[6] or asymmetric catalysts^[7][8] have been developed.^[9]

[edit] Reaction mechanism

[edit] References

1. ↑  Strecker, A. Ann. 1850, 75, 27.
2. ↑  Strecker, A. Ann. 1854, 91, 349.
3. ↑  Kendall, E. C.; McKenzie, B. F. Organic Syntheses, Coll. Vol. 1, p.21 (1941); Vol. 9, p.4 (1929). (Article)
4. ↑  Clarke, H. T.; Bean, H. J. Organic Syntheses, Coll. Vol. 2, p.29 (1943); Vol. 11, p.4 (1931). (Article)
5. ↑  Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125(19), 5634-5635. (DOI:10.1021/ja034980+)
6. ↑  Davis, F. A. et al. Tetrahedron Lett. 1994, 35, 9351.
7. ↑  Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122(5), 762-766. (DOI:10.1021/ja9935207)
8. ↑  Huang, J.; Corey, E. J. Org. Lett. 2004, 6(26), 5027-5029. (DOI:10.1021/ol047698w)
9. ↑  Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650. (Review, DOI:10.1016/S0040-4020(01)80840-1)

[edit] See also

• Bucherer-Bergs reaction