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). 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.
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.
The traditional Strecker synthesis gives racemic α-amino nitriles, but recently several procedures utilizing asymmetric auxiliaries or asymmetric catalysts have been developed.
[edit] Reaction mechanism
[edit] References
- ↑ Strecker, A. Ann. 1850, 75, 27.
- ↑ Strecker, A. Ann. 1854, 91, 349.
- ↑ Kendall, E. C.; McKenzie, B. F. Organic Syntheses, Coll. Vol. 1, p.21 (1941); Vol. 9, p.4 (1929). (Article)
- ↑ Clarke, H. T.; Bean, H. J. Organic Syntheses, Coll. Vol. 2, p.29 (1943); Vol. 11, p.4 (1931). (Article)
- ↑ Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125(19), 5634-5635. (DOI:10.1021/ja034980+)
- ↑ Davis, F. A. et al. Tetrahedron Lett. 1994, 35, 9351.
- ↑ Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122(5), 762-766. (DOI:10.1021/ja9935207)
- ↑ Huang, J.; Corey, E. J. Org. Lett. 2004, 6(26), 5027-5029. (DOI:10.1021/ol047698w)
- ↑ Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650. (Review, DOI:10.1016/S0040-4020(01)80840-1)
[edit] See also
- Bucherer-Bergs reaction
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