Efficient asymmetric synthesis of (S)-2-methylasparagine

Synlett

Volumn , Issue 10, 1998, Pages 1099-1101

  Aoyagi, Yutaka ^a   Williams, Robert M ^a  

^a Veterinary Dentistry and Oral Surgery   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002550810     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1884     Document Type: Article

References (20)

1. For a review of asymmetric synthesis of α-amino acids, see: Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989: Vol 7.
2. Saari, W. S.; Freedman, M. B; Hartman, R. D.; King, S. W.; Raab, A. W.; Randall, W. C.; Engelhardt, E. L.; Hirschmann, R.; Rosegay, Ludden, C. T.; Scriabine, A. J. Med. Chem. 1978, 21, 746.
3. Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. G.; Gaul, S. L.; Sweet, C. S. D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. G.; Gaul, S. L.; Sweet, C. S. J. Med. Chem. 1984, 27, 713.
4. Ramalingam, K.; Woodard, R. W. Tetrahedron Lett. 1985, 1135.
5. Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc. 1980, 102, 7136.
6. Paul, P. K.; Sukumar, M.; Bardi, R.; Piazzesi, A.M.; Valle, G.; Toniolo, C.; Balaram, P. J. Am. Chem. Soc. 1986, 108, 6363.
7. Yuan, C.; Williams, R. M. J. Am. Chem. Soc. 1997, 119, 11777.
8. Katayama, N.; Fukusumi, S.; Funabashi, Y.; Iwai, T.; Ono, H. J. Antibiot. 1993, 46, 606.
9. Funabashi, Y.; Tsubotani, S.; Koyama, K.; Katayama, N.; Harada, S. Tetrahedron 1993, 49, 13.
10. Williams, R. M.; Im, M. -N. Tetrahedron 1988, 29, 6075.
11. Williams, R. M.; Im, M. -N. J. Am. Chem. Soc. 1988, 29, 6075.
12. Bender, D. M.; Williams, R. M. J. Org. Chem. 1997, 62, 6690 and references cited herein.
13. The requisite diphenyloxazines 1 utilized to prepare compounds 4 and 6 are commercially available from Aldrich Chemical Co.; (-)-1: catalog #33187-2 (CAS Registry #100516-54-9); the antipode of (+)-1: Catalog #33185-6 (CAS Registry #105228-46-4).
14. Baldwin, J. E.; Lee, V.; Schofield, C. J. Synlett 1992, 249.
15. 6: C, 72.21; H, 6.45; N, 2.72. Found: C, 72.40; H, 6.43; N, 2.75.
16. 6: C, 71.84; H, 6.23; N, 2.79. Found: C, 71.70; H, 6.00; N, 2.79.
17. 6 for 516.2386. Found: 516.2402.
18. Nozaki, S.; Muramatsu, I. Bull. Chem. Soc. Jpn. 1988, 61, 2647.
19. ++H): 459.1920. Found: 459.1937.
20. ++H): 147.0770. Found: 147.0774.