Transformation of l-phenylalanine to (S)-indoline-2-carboxylic acid without group-protection

Research on Chemical Intermediates

Volumn 39, Issue 3, 2013, Pages 1143-1152

  Liu, Jin Qiang ^a   Chen, Xin Zhi ^b   Ji, Baoming ^a   Zhao, Bang Tun ^a  

^a LUOYANG NORMAL UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

(S) Indoline 2 carboxylic acid; 2,4 Dinitro l phenylalanine; Chiral pool; Group protection free; l Phenylalanine; Nitro amination; One pot

Indexed keywords

2,4-DINITRO-L-PHENYLALANINE; CHIRAL POOL; GROUP-PROTECTION-FREE; L-PHENYLALANINE; ONE POT;

AMINES; CARBOXYLIC ACIDS; LAKES; NITRATION; UREA;

AMINO ACIDS;

EID: 84876465201     PISSN: 09226168     EISSN: 15685675     Source Type: Journal    
DOI: 10.1007/s11164-012-0673-z     Document Type: Article

References (30)

1. J.Q. Liu, C. Qian, X.Z. Chen, Chin. J. Org. Chem. 31, 634 (2011)
2. R. Viswanathan, E.N. Prabhakaran, M.A. Plotkin, J.N. Johnston, J. Am. Chem. Soc. 125, 163 (2002)
3. C.J. Vickers, T.-S. Mei, J.-Q. Yu, Org. Lett. 12, 2511 (2010)
4. G. He, Y. Zhao, S. Zhang, C. Lu, G. Chen, J. Am. Chem. Soc. 134, 3 (2012)
5. J.Q. Liu, C. Qian, X.Z. Chen, Synthesis 3, 403 (2010)
6. M. Kumar, V. Prashar, S. Mahale, M.V. Hosur, Biochem. J. 389, 365 (2005)
7. L.A. MacMillan-Crow, J.A. Thompson, Arch. Biochem. Biophys. 366, 82 (1999)
8. T. Kersebohm, S.I. Kirin, N. Metzler-Nolte, Bioorg. Med. Chem. Lett. 16, 2964 (2006)
9. C. Robledoluiggi, W.D. Wilson, E. Pares, M. Vera, C.S. Martinez, D. Santiago, Biopolymers 31, 907 (1991)
10. C. Henze, C. Earl, E. Sautter, N. Schmidt, C. Themann, A. Hartmann, W.H. Oertel, Brain Res. 1052, 97 (2005)
11. J.M. Ghuysen, Bacteriol. Rev. 32, 425 (1968)
12. A.M. ElWaziry, Y. Tomita, J.R. Ling, R. Onodera, J. Chromatogr. B. 677, 53 (1996)
13. M. Zanol, L. Gastaldo, J. Chromatogr. 536, 211 (1991)
14. C.H. Kruse, K.G. Holden, P.H. Offen, M.L. Pritchard, J.A. Feild, D.J. Rieman, P.E. Bender, B. Ferguson, R.G. Greig, G. Poste, J. Med. Chem. 31, 1768 (1988)
15. B.M. Katz, L.J. Lundquist, D.A. Walsh, D.B. Glass, Int. J. Peptide Protein Res. 33, 439 (1989)
16. L.M. De Leon-Rodriguez, Z. Kovacs, A.D. Sherry, Lett. Org. Chem. 2, 160 (2005)
17. M. Sassatelli, E. Debiton, B. Aboab, M. Prudhomme, P. Moreau, Eur. J. Med. Chem. 41, 709 (2006)
18. P.N. Rao, D.M. Peterson, C.K. Acosta, M.L. Bahr, H.K. Kim, Org. Prep. Proc. Int. 23, 103 (1991)
19. J.-Q. Liu, C. Qian, T. Zhang, X.-Z. Chen, J Chem. Eng. Chin. Univ. 2009, 23 (1007)
20. R.J. Block, D. Bolling, J. Biol. Chem. 129, 1 (1939)
21. R. Kapeller-Alder, Biochem. Zeitschrift 252, 185 (1932)
22. C.T. Beer, F. Dickens, D. Salmony, Biochem. J. 49, 700 (1951)
23. D. Monnier, R. Guerne, Anal. Chim. Acta 19, 90 (1958)
24. J.Q. Liu, C. Qian, X.Z. Chen, Prog. Chem. 21, 2635 (2009)
25. J. Almog, A. Klein, A. Sokol, Y. Sasson, D. Sonenfeld, T. Tamiri, Tetrahedron Lett. 47, 8651 (2006)
26. C. Qian, J.Q. Liu, X. Z. Chen, J. Chem. Res. 70 (2008)
27. Qianchao, J.Q. Liu, X.Z. Chen, Synth. Commun. 38, 2782 (2008)
28. T. Horaguchi, T. Oyanagi, E.C. Creencia, K. Tanemura, T.J. Suzuki, Heterocycl. Chem. 41, 1 (2004)
29. F. Bergel, J.A. Stock, J. Chem. Soc. 2409 (1954)
30. S.N. Lavrenov, S.A. Lakatosh, L.N. Lysenkova, A.M. Korolev, M.N. Preobrazhenskaya, Synthesis 3, 320 (2002)