One-pot sequence for the decarboxylation of α-amino acids

Synlett

Volumn , Issue 4, 2003, Pages 542-546

  Laval, Gilles ^a   Golding, Bernard T ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

Amine; Decarboxylation; Nitrile; amino acid

Indexed keywords

ALPHA AMINO ACID; AMMONIUM CHLORIDE; N BROMOSUCCINIMIDE; NICKEL CHLORIDE; NITRILE; SODIUM BOROHYDRIDE; WATER;

ADDITION REACTION; AMINO ACID SEQUENCE; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DECARBOXYLATION; PH; SYNTHESIS;

EID: 0037237166     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37512     Document Type: Article

References (24)

1. Curtius, T.; Lederer, A. Chem. Ber. 1886, 19, 2462.
2. See for example: (a) Pasini, A.; Zunio, F. Angew. Chem., Int. Ed. Engl. 1987, 26, 615. (b) Miyadera, T.; Sugimura, Y.; Hashimoto, T.; Tanaka, T.; Iino, K.; Shibata, T.; Sugawara, S. J. Antibiotics 1983, 36, 1034.
3. See for example: (a) Pasini, A.; Zunio, F. Angew. Chem., Int. Ed. Engl. 1987, 26, 615. (b) Miyadera, T.; Sugimura, Y.; Hashimoto, T.; Tanaka, T.; Iino, K.; Shibata, T.; Sugawara, S. J. Antibiotics 1983, 36, 1034.
4. See for example: Martens, J. Top. Curr. Chem. 1984, 125, 165.
5. Chatelus, G. Bull. Soc. Chim. Fr. 1964, 2533.
6. (a) Hashimoto, M.; Eda, Y.; Osanai, Y.; Iwai, T.; Aoki, S. Chem. Lett. 1986, 6, 893.
7. (b) Wallbaum, S.; Mehler, T.; Martens, J. Synth. Commun. 1994, 24, 1381.
8. (a) Boeker, E. A.; Snell, E. E. In The Enzymes, 3rd ed. Vol. 6; Boyer, P. D., Ed.; Academic Press: New York, 1972, 217-254.
9. (b) Werle, E. Angew. Chem. 1951, 63, 550.
10. (c) Gale, E. F. Adv. Enzymol. 1946, 6, 1.
11. (a) Nakai, H.; Kanaoka, Y. Synthesis 1982, 141.
12. (b) Flemming, K. Strahlentherapie 1964, 123, 457.
13. (c) Photochemical decarboxylation of N-arenesulfonyl amino acids: Papageorgiou, G.; Corrie, J. E. T. Tetrahedron 1999, 237.
14. Kametani, T.; Takano, S.; Hibino, S.; Takeshita, M. Synthesis 1972, 475.
15. (a) Rossen, K.; Simpson, P. M.; Wells, K. Synth. Commun. 1993, 23, 1071.
16. (b) Kanao, S.; Shinozuka, S. J. Pharm. Soc. Jpn. 1947, 67, 218.
17. Laval, G.; Clegg, W.; Crane, C. G.; Hammershøi, A.; Sargeson, A. M.; Golding, B. T. Chem. Commun. 2002, 1874.
18. (a) Gowda, B. T., Mahadevappa, D. S. J. Chem. Soc., Perkin Trans. 2 1983, 323.
19. (b) For the oxidative decarboxylation of N-protected amino acids see for example: Boto, A.; Hernandez, R.; De Leon, Y.; Suarez, E. J. Org. Chem. 2001, 66, 7796.
20. Gopalakrishnan, G.; Hogg, J. L. J. Org. Chem. 1985, 50, 1206.
21. Satoh, T.; Suzuki, S. Tetrahedron Lett. 1969, 4555.
22. 4. Removal of the solvent afforded 2-phenylethylamine (9a) (208 mg, 71%) as a colourless oil.
23. 4. Removal of the solvent afforded 2-phenylethylamine (9a) (208 mg, 71%) as a colourless oil.
24. Amino alcohol 15 is a building block for the synthesis of the antidepressant fluoxetine: Hilborn, J. W.; Lu, Z.-H.; Jurgens, A. R.; Fang, Q. K.; Byers, P.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2001, 8919.