Synthesis of optically active 1,1'-ferrocenylene-bis-alanine carrying four different protecting groups

Tetrahedron Asymmetry

Volumn 8, Issue 11, 1997, Pages 1841-1846

  Basu, Basudeb ^a   Chattopadhyay, Shital K ^a   Ritzén, Andreas ^a   Frejd, Torbjörn ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031006996     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00190-0     Document Type: Article

References (22)

1. Williams, R. M.; Hedrix, J. A. Chem. Rev., 1992, 92, 889-917.
2. Rao, A. V. R.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev., 1995, 95, 2135-2167.
3. Burley, S. K.; Petsko, G. A. J. Am. Chem. Soc., 1986, 108, 7995-8001.
4. Burley, S. K.; Wang, A. H.-J.; Votano, J. R.; Rich, A. Biochemistry, 1987, 26, 5091-5099.
5. Burley, S. K.; Petsko, G. A. TIBTECH, 1989, 7, 354-359.
6. Singh, J.; Thornton, J. M. FEBS Lett., 1985, 797, 1-6.
7. Muehldorf, A. V; Van Engen, D.; Warner, J. C; Hamilton, A. D. J. Am. Chem. Soc., 1988, 110, 6561-6562.
8. Carlström, A. S.; Frejd, T. J. Org. Chem., 1990, 55, 4175.
9. Jackson, R. F. W.; Turner, D.; Block, M. H. Synlett, 1996, 862-864.
10. Schmidt, U.; Lieberknecht, A.; Schanbacher, U.; Beuttler, T.; Wild, J. Angew. Chem. Int. Ed. Engl., 1982, 21, 770.
11. Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis, 1984, 53-60.
12. Shimohigashi, Y.; Nitz, T. J.; Stammer, C. H.; Inubishi, T. Tetrahedron Lett., 1982, 23, 3235-3236.
13. Nogrady, M. Stereoselective synthesis. In Stereoselective synthesis.; VCH: Weinheim, 1987; pp. 77-79.
14. Koenig, K. E. The Applicability of Asymmetric Homogeneous Catalytic Hydrogenation. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press, Inc.: New York, 1985; Vol. 5; pp. 71-101.
15. For simplicity, the notations (±)-6 and (±)-8 are taken to mean racemic, diastereomeric mixtures of all stereoisomers of 6 and 8.
16. Ojima, I. Pure and Applied Chem., 1984, 56, 99-110.
17. Poulin, J.-C; Kagan, H. B. J. C. S. Chem. Commun., 1982, 1261-1262.
18. Mangold, R. Stereoselektive Synthese der nichtproteinogenen Aminosäuren (2S,3R)-3-Methylarginin und erythro-4-Hydroxy-L-lysin., Thesis, University of Stuttgart 1991.
19. Carlström, A. S.; Frejd, T. Synthesis, 1989, 414-418.
20. Mueller-Westerhoff, U. T; Yang, Z.; Ingram, G. J. Organomet. Chem., 1993, 463, 163-167.
21. Balavoine, G. G. A.; Doisneau, G.; Fillebeen-Khan, T. J. Organomet. Chem., 1991, 412, 381-382.
22. Kovar, R. F; Rausch, M. D.; Rosenberg, H. Organometal. Chem. Synth., 1970/1971, 1, 173.