Organoboranes for synthesis. 16. A convenient synthesis of enantiomerically pure isopinocampheylamine, a chiral derivatizing agent for gas chromatographic analysis of optically active carboxylic acids

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 341-345

  Ramachandran, P Veeraraghavan ^a   Rangaishenvi, Milind V ^a,b   Singaram, Bakthan ^a,c   Goralski, Christian T ^a,d   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

^b Astra Research Centre India   (India)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d DOW CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CAMPHOR DERIVATIVE; CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DERIVATIZATION; DRUG IDENTIFICATION; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; TECHNIQUE;

EID: 0000096849     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9512158     Document Type: Article

References (27)

1. Thalidomide is a tragic example of one optical isomer being a safe drug, whereas the other is a potent mutagen. Phocomelia, a teratogenic effect characterized by the absence of arms and legs, is ascribed exclusively to the S-isomer. Blaschke, G.; Kraft, H. P.; Fickentseher, K.; Koehler, F. Arzneim.-Forsch. 1979, 29, 1640.
2. Stinson, S. C. Chem. Eng. News 1992, 70(39), 46.
3. The wide use of a chiral amine, for example α-methylbenzylamine, is evident from the large number of references in the literature. A CAS ONLINE (American Chemical Society) search for (S)-α-methylbenzylamine (Registry No. 2627-86-3) showed ∼1500 references and (R)-α-methylbenzylamine (Registry No. 3886-69-9) showed ∼1300 references.
4. Bussche-Hunnefeld, C. v d.; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795.
5. Sugasawa, T.; Toyoda, T. Tetrahedron Lett. 1979, 1423.
6. Kitamoto, M.; Hiroi, K.; Terashima, S.; Yamada, S. Chem. Pharm. Bull. 1974, 22, 459.
7. Bertz, S. H.; Dabbagh, G.; Sundararajan, G. J. Org. Chem. 1986, 51, 4953.
8. Yamaguchi, K., Yamada, N.; Minoura, Y. Polymer 1973, 14, 427.
9. Fiorini, M.; Giongo, G. M. J. Mol. Catal. 1979, 5, 303.
10. Brown, H. C.; Ramachandran, P. V. J. Organomet. Chem. 1995, 500, 1.
11. (a) Brown, H. C.; Heydkamp, W. R.; Breuer, E.; Murphy, W. S. J Am. Chem. Soc. 1964, 86, 3365.
12. (b) Rathke, M. W.; Inoue, N.; Varma, K. R.; Brown, H. C. Ibid. 1966, 88, 2870.
13. (a) Thome, L. G. Chem. Ber. 1903, 36, 582.
14. (b) Holm, R. H.; Chakravorty, A.; Dudek, G. O. J. Am. Chem. Soc. 1964, 86, 379.
15. (a) Santaniello, E.; Casati, R.; Milani, F. J. Chem. Soc., Perkin Trans. 1 1985, 919.
16. Brown, H. C.; Kim, K. W.; Srebnik, M.; Singaram, B. Tetrahedron 1987, 43, 4071.
17. Brown, H. C.; Kim, K. W.; Cole, T. E.; Singaram, B. J. Am. Chem. Soc 1986, 108, 6761.
18. Brown, H. C.; Chandrasekharan, J., Ramachandran, P. V. J. Am Chem. Soc. 1988, 110, 1539. DIP-Chloride is a trademark of the Aldrich Chemical Co.
19. Suplecowax and SPB-5 are trademarks of Supelco (b) The methylsilicone column was purchased from Hewlett-Packard.
20. Paul, R.; Anderson, G. W. J. Org. Chem. 1962, 27, 2094.
21. (a) Acharya, S. P.; Brown, H. C. J. Am. Chem. Soc. 1967, 89, 1925.
22. (b) Brown, H. C.; Suzuki, A. J. Am. Chem. Soc. 1967, 89, 1933.
23. (c) Acharya, S. P.; Brown, H. C.; Suzuki, A.; Nozawa, S.; Itoh, M. J. Org. Chem. 1969, 34, 3015.
24. (d) Acharya, S. P.; Brown, H. C. J. Org. Chem. 1970, 35, 196.
25. (e) Acharya, S. P.; Brown, H. C. J. Org. Chem. 1970, 35, 3874.
26. (f) Brown, H. C.; Pfaffenberger, C. D. Tetrahedron 1975, 31, 625.
27. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Syntheses via Boranes; Wiley-Interscience: New York, 1975; Chapter 9.