Palladium-catalyzed synthesis of novel optically active tryptophan analogues

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1717-1720

  Van Esseveldt, Bart C J ^a   Van Delft, Floris L ^a   De Gelder, René ^a   Rutjes, Floris P J T ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; AMINO ACID; ANILINE; PALLADIUM; PROLINE DERIVATIVE; TRYPTOPHAN DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; OPTICS; PRECURSOR; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0141852845     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034360d     Document Type: Article

References (23)

1. (a) Cady, S. G.; Sono, M. Arch. Biochem. Biophys. 1991, 292, 326.
2. (b) Peterson, A. C.; Migawa, M. T.; Martin, M. J.; Hamaker, L. K.; Czerwinski, K. M.; Zhang, W.; Arend, R. A.; Fisette, P. L.; Ozaki, Y.; Will, J. A.; Brown, R. R.; Cook, J. M. Med. Chem. Res. 1994, 3, 531.
3. (c) Southan, M.; Truscott, R.; Jamie, J.; Pelosi, L.; Walker, M.; Maeda, H.; Iwamoto, Y.; Tone, S. Med. Chem. Res. 1996, 5, 343.
4. (a) Ma, C.; Yu, S.; He, X.; Liu, X.; Cook, J. M. Tetrahedron Lett. 2000, 41, 2781.
5. (b) Ma, C.; Liu, X.; Li, X.; Flippen-Anderson, J.; Yu, S.; Cook, J. M. J. Org. Chem. 2001, 66, 4525.
6. Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277.
7. Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1997.
8. (a) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339.
9. (b) Grigg, R.; Savic, V. J. Chem. Soc., Chem. Commun. 2000, 873.
10. (a) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
11. (b) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem 1998, 63, 7652.
12. (c) Cacchi, S.; Carcinelli, V.; Marinelli, F. J. Organomet. Chem. 1994, 475, 289.
13. (d) Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1989, 54, 5856.
14. (a) Wolf, L. B.; Tjen, K. C. M. F.; Ten Brink, H. T.; Blaauw, R. H.; Hiemstra, H.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2002, 344, 70.
15. (b) Wolf, L. B.; Tjen, K. C. M. F.; Rutjes, F. P. J. T.; Hiemstra, H.; Schoemaker, H. E. Tetrahedron Lett. 1998, 39, 5081.
16. For a review on applications of unsaturated amino acids, see: Rutjes, F. P. J. T.; Wolf, L. B.; Schoemaker, H. E. J. Chem. Soc, Perkin Trans. 1 2000, 4197.
17. In this article, referred to as propargylglycine; 2-amino-5-hexynoic acid is homopropargylglycine, etc.
18. (a) Wolf, L. B.; Sonke, T.; Tjen, K. C. M. F.; Kaptein, B.; Broxterman, Q. B.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2001, 343, 662.
19. (b) Sonke, T.; Kaptein, B.; Boesten, W. H. J.; Broxterman, Q. B.; Kamphuis, J.; Formaggio, F.; Toniolo, C.; Rutjes, F. P. J. T.; Schoemaker, H. E. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker: New York, 2000; p 23.
20. Crisp, G. T.; Robinson, T. A. Tetrahedron 1992, 48, 3239.
21. Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 203097.
22. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2002.
23. For similar regioselective Pd-catalyzed hydration of substituted acetylenes, see: Imi, K.; Imai, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 3127.