A novel approach to homochiral β-amino acids 1

Tetrahedron Letters

Volumn 37, Issue 18, 1996, Pages 3165-3168

  Seki, Masahiko ^a   Matsumoto, Kazuo ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0029959913     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00518-7     Document Type: Article

References (27)

1. Synthesis of Amino Acids and Related Compounds. 46. Part 45: Seki, M.; Matsumoto, K.; Biosci. Biochem. Biotech. in press.
2. Suda, H.; Takita, T.; Aoyagi, T.; Umezawa, H. J. Antibiot. 1976, 29, 100-101.
3. (a) Chaturved, N. C.; Park, W. K.; Smeby, R. P.; Bumpus, K. M. J. Med. Chem. 1970, 13, 177-181.
4. (b) Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y. J. Chem. Soc. Chem. Commun. 1989, 1678-1680.
5. (c) Okino, T.; Matsuda, H.; Murakami, M.; Yamaguchi, K. Tetrahedron Lett 1993, 34, 501-504.
6. Bovy, P. R.; Tjoeng, F. S.; Rico, J. G.; Rogers, T. E.; Lindmark, R. J.; Zablocki, J. A.; Garland, R. B.; McMackins, D. E.; Dayringer, H.; Toth, M. V.; Zupec, M. E.; Rao, S.; Panzer-Knodle, S. G.; Nicholson, N. S.; Salyers, A.; Taite, B. B.; Herin, M.; Miyano, M.; Feigen, L. P.; Adams, S. P. Bioorg. Med. Chem. 1994, 2, 881-895.
7. Denis, J. N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959.
8. For a review see: Cole, D. C. Tetrahedron 1994, 50, 9517-9582.
9. For reviews on the utilization of aspartic acid to drug-synthesis see: (a) Matsumoto, K.; Seki, M. J. Syn. Org. Chem. Jpn 1991, 49, 26-41.
10. (b) Seki, M.; Matsumoto, K. Bioindustry 1995, 12(6), 5-19.
11. (a) Gmeiner, P. Tetrahedron Lett. 1990, 31, 5717-5720.
12. (b) El Marini, A.; Roumestant, M. L.; Viallefont, P.; Razafindramboa, D.; Bonato, M.; Follet, M. Synthesis 1992, 1104.
13. (c) Jefford, C. W.; Wang, J. Tetrahedron Lett. 1993, 34, 1111-1114.
14. Sugano, H.; Miyoshi, M. Bull. Chem. Soc. Jpn 1973, 46, 669-670.
15. Hoffmann, M. G,; Zeiss, H.-J. Tetrahedron Lett. 1992, 33, 2669-2672.
16. Synthesis of optically pure α-aminoketones from amide derivatives of α-amino acids, see: (a) Cupps, T. L.; Boutin, R. H.; Rapoport, H. J. Org. Chem. 1985, 50, 3972-3979.
17. (b) Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320-5327.
18. (c) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5415-5421.
19. (a) Basha, A.; Lipton, M. F.; Weinreb, S. M. Tetrahedron Lett. 1977, 4171-4174.
20. (b) Lipton, M. F.; Basha, A.; Weinreb, S. M. Organic Synthesis; Wiley: New York, 1980, vol. 59, 49-53.
21. (c) Garigipati, R. S.; Weinreb, S. M. J. Org. Chem. 1988, 53, 4143-4145.
22. 3: MeOH=20:1) to afford 4a (835 mg, 85%) in colorless crystals. cis/trans=4.1/1. mp 98-100°C. 4b: cis/trans=4.5/1. mp 79-80°C. 4c: cis/trans=6/1. mp 99-101°C. 4d: cis/trans=5/1. mp 92-94°C. 4e: cis/trans=6/1. mp98-101°C. 4f: cis/trans=3/1. oil.
23. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
24. 25 -4.4° (c, 0.23, MeOH).
25. (a) Birkofer, L.; Bierstein, E.; Ritter, F. Chem. Ber. 1961, 94, 821-828.
26. (b) Sakaitani, M.; Hori, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 2983-2984.
27. 25 +12.9° (c, 0.55, MeOH).