Chemoenzymatic syntheses of two optically active hexa-azamacrocycles

Tetrahedron Asymmetry

Volumn 10, Issue 2, 1999, Pages 367-374

  Alfonso, Ignacio ^a   Rebolledo, Francisca ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE 1,2 DIAMINE BIS(AMIDOESTER) DERIVATIVE; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; MOLECULAR RECOGNITION; PRIORITY JOURNAL; PROTON TRANSPORT; SYNTHESIS;

EID: 0033613893     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00010-5     Document Type: Article

References (35)

1. (a) Lehn, J. M. Supramolecular Chemistry, VCH: Weinheim, 1995;
2. (b) Bianchi, A.; Bowman-James, K.; García-España, E. The Supramolecular Chemistry of Anions, VCH: Weinheim, 1997;
3. (c) Dietrich, B. Pure Appl. Chem. 1993, 65, 1457-1464;
4. (d) Seel, C.; Galán, A.; de Mendoza, J. Top. Curr. Chem. 1995, 175, 102-132;
5. (e) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1995, 97, 1609-1646.
6. Izatt, R. M.; Pawlak, K.; Bradshaw, S. S.; Bruening, R. L. Chem. Rev. 1995, 95, 2529-2586.
7. (a) Dietrich, B.; Hosseini, M. W.; Lehn, J. M.; Sessions, R. B. J. Am. Chem. Soc. 1981, 103, 1282-1283;
8. (b) Hosseini, M. W.; Lehn, J. M. Helv. Chim. Acta. 1986, 69, 587-603;
9. (c) Hosseini, M. W.; Lehn, J. M. Helv. Chim. Acta. 1988, 71, 749-756.
10. (a) Kimura, E.; Sakonaka, A.; Yatsunami, T.; Kodama M. M. J. Am. Chem. Soc. 1981, 103, 3041-3045;
11. (b) Kimura, E.; Kodama, M.; Yatsunami, T. M. J. Am. Chem. Soc. 1982, 104, 3182-3187;
12. (c) Kimura, E.; Sakonaka, A. J. Am. Chem. Soc. 1982, 104, 4984-4985;
13. (d) Kimura, E.; Kuramoto, Y.; Koike, T.; Fujioka, H.; Kodama, M. J. Org. Chem. 1990, 55, 42-46.
14. (a) Bencini, A.; Bianchi, A.; Burguete, M. I.; García-España, E.; Luis, S. V. J. Am. Chem. Soc. 1992, 114, 1919-1920;
15. (b) Bencini, A.; Bianchi, A.; Burguete, M. I.; Dapporto, P.; Doménech, A.; García-España, E.; Luis, S. V.; Paoli, P.; Ramírez, J. A. J. Chem. Soc., Perkin Trans. 2 1994, 114, 569-577
16. (a) Siegel, G. J.; Agranoff, B. W.; Albers, R. W.; Molinoff, P. B. Basic Neurochemistry: Molecular, Cellular and Medical Aspects, 5th Edn; Raven Press: New York, 1994; pp. 367-387;
17. (b) Yeh, J. I.; Biemann, H. P.; Prive, G. G.; Pandit, J.; Koshland Jr., D. E.; Kim, S. H. J. Mol. Biol. 1996, 262, 186-201.
18. Stryer, L. Biochemistry, W. H. Freeman and Company: New York, 1988.
19. For chiral recognition of dicarboxylic acids, but not dicarboxylate anions, see: Lustenberger, P.; Martinborough, E.; Mordasini-Denti, T.; Diederich, F. J. Chem. Soc., Perkin Trans. 2 1998, 747-761, and references cited therein.
20. Sessler, J. L.; Andrievsky, A.; Kral, V.; Lynch, V. J. Am. Chem. Soc. 1997, 119, 9385-9392.
21. For some recent applications see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (b) Palucki, M.; Finney, N. S.; Pospisil, P. J.; Güler, M. L.; Ishida, T.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 948-954; (c) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105; (d) Schaus, S. E.; Branalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403-405.
22. For some recent applications see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (b) Palucki, M.; Finney, N. S.; Pospisil, P. J.; Güler, M. L.; Ishida, T.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 948-954; (c) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105; (d) Schaus, S. E.; Branalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403-405.
23. For some recent applications see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (b) Palucki, M.; Finney, N. S.; Pospisil, P. J.; Güler, M. L.; Ishida, T.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 948-954; (c) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105; (d) Schaus, S. E.; Branalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403-405.
24. For some recent applications see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816; (b) Palucki, M.; Finney, N. S.; Pospisil, P. J.; Güler, M. L.; Ishida, T.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 948-954; (c) Trost, B. M.; Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104-1105; (d) Schaus, S. E.; Branalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403-405.
25. (a) Farrell, N.; Kiley, D. M.; Schmidt, W.; Hacker, M. P. Inorg. Chem. 1990, 29, 397-403;
26. (b) Skog, K.; Wennerström, O. Tetrahedron Lett. 1992, 33, 1751-1754;
27. (c) Still, W. C. Acc. Chem. Res. 1996, 29, 155-163;
28. (d) Reedijk, J. J. Chem. Soc., Chem. Commun. 1996, 801-806;
29. (e) Pan, Z.; Still, W. C. Tetrahedron Lett. 1996, 37, 8699-8702;
30. (f) Gasparrini, F.; Misiti, D.; Still, W. C.; Villani, C.; Wennemers, H. J. Org. Chem. 1997, 62, 8221-8224.
31. Alfonso, I.; Astorga, C.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Chem. Commun. 1996, 2471-2472.
32. Bridger, G. J.; Skerlj, R. T.; Padmanabhan, S.; Thornton, D. J. Org. Chem. 1996, 61, 1519-1522.
33. (a) Richman, J. E.; Atkins, T. J. J. Am. Chem. Soc. 1974, 96, 2268-2270;
34. (b) Vriesema, B. K.; Butler, J.; Kellog, R. M. J. Org. Chem. 1984, 49, 110-113.
35. Dietrich, B.; Hosseini, M. W.; Lehn, J. M.; Sessions, R. B. Helv. Chim. Acta 1983, 66, 1262-1278.