(S)-Pyroglutamic acid, (S)-malic acid, and (S)-serine as useful starting materials in the synthesis of enantiopure hydroxyamidines

European Journal of Organic Chemistry

Volumn , Issue 1, 2000, Pages 115-124

  Ostendorf, Martin ^a   Dijkink, Jan ^a   Rutjes, Floris P J T ^a   Hiemstra, Henk ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Amidines; Chiral base; Chiral pool; Enantioselective catalysis; N Acyliminium ions

Indexed keywords

ALCOHOL; AMIDINE; HYDROXYL GROUP; LACTAM DERIVATIVE; MALIC ACID; PYROGLUTAMIC ACID; SERINE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 0033986185     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200001)2000:1<115::aid-ejoc115>3.0.co;2-j     Document Type: Article

References (30)

1. The Chemistry of Amidines and Imidates (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1991, vol. 1 and 2.
2. [2a] M. A. Convery, A. P. Davis, C. J. Dunne, J. W. MacKinnon, J. Chem. Soc., Chem. Commun. 1994, 2557-2558.
3. [2b] M. A. Convery, A. P. Davis, C. J. Dunne, J. W. MacKinnon, Tetrahedron Lett. 1995, 36, 4279-4282.
4. [3a] G. Papandreou, M. K. Tong, B. Ganem, J. Am. Chem. Soc. 1993, 115, 11682-11690.
5. [3b] Y. Blériot, A. Genre-Grandpierre, C. Tellier, Tetrahedron Lett. 1994, 35, 1867-1870.
6. J. Dijkink, K. Goubitz, M. N. A. Van Zanden, H. Hiemstra, Tetrahedron: Asymmetry 1996, 7, 515 -524.
7. M. Ostendorf, S. van der Neut, F. P. J. T. Rutjes, H. Hiemstra, Eur. J. Org. Chem. 2000, 105-113, preceding paper.
8. [6a] W. J. Klaver, H. Hiemstra, W. N. Speckamp, J. Am. Chem. Soc. 1989, 111, 2588-2595.
9. [6b] S. Louwrier, M. Ostendorf, A. Boom, H. Hiemstra, W. N. Speckamp, Tetrahedron 1996, 52, 2603-2628.
10. G. M. Coppola, H. F. Schuster, Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids, Wiley, New York, 1987, chapter 4.
11. S. Saijo, M. Wada, J. Himizu, A. Ishida, Chem. Pharm. Bull. 1980, 28, 1449-1452.
12. S. Kanao, S. Inagawa, J. Pharm. Soc. Jpn. 1928, 48, 238-245.
13. F. G. Fang, M. Prato, G. Kim, S. J. Danishefsky, Tetrahedron Lett. 1989, 30, 3625-3628.
14. [11a] A. G. M. Barrett in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, vol. 8, pp. 251-252.
15. [11b] A. Echavarren, A. Galán, J. de Mendoza, A. Salmerón, J.-M. Lehn, Helv. Chim. Acta 1988, 71, 685-693.
16. [11c] J. O. Osby, S. W. Heinzman, B. Ganem, J. Am. Chem. Soc. 1986, 108, 67-72.
17. B. Yde, N. M. Yousif, U. Pedersen, I. Thomsen, S.-O. Lawesson, Tetrahedron 1984, 40, 2047-2052.
18. [13a] H. E. Zaug, D. L. Arendsen, R. S. Egan, J. Heterocycl. Chem. 1979, 16, 21 -30.
19. [13b] J. J. J. de Boer, Reactions with ω-Carbinollactams, Ph.D. Thesis, University of Amsterdam, 1979.
20. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1991.
21. [15a] D. H. R. Barton, W. B. Motherwell, Pure Appl. Chem. 1981, 53, 15-31.
22. [15b] W. Hartwig, Tetrahedron 1983, 39, 2609-2645.
23. [15c] M. J. Robins, J. S. Wilson, F. Hanske, J. Am. Chem. Soc. 1983, 105, 4059-4065.
24. J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543-2549.
25. K. C. Nicolaou, M. E. Bunnage, K. Koide, J. Am. Chem. Soc. 1994, 116, 8402-8403.
26. F. L. Cook, C. W. Bowers, C. L. Liotta, J. Org. Chem. 1974, 39, 3416-3418.
27. J. B. P. A. Wijnberg, H. E. Schoemaker, W. N. Speckamp, Tetrahedron 1978, 34, 179-187.
28. J. C. Hubert, J. B. P. A Wijnberg, W. N. Speckamp, Tetrahedron 1975, 31, 1437-1441.
29. H. Hiemstra, H. Wynberg, J. Am. Chem. Soc. 1981, 103, 417-430.
30. Experimental details and full structural data for the structure determination of 6 are submitted as a CIF-access paper to Acta Crystallogr., Sect. C (Kooÿman, Spek, 1999).