Chemoenzymatic preparation of optically active β-amino-cyclohexanols and their application in the enantioselective addition of diethylzinc to benzaldehyde

Tetrahedron Asymmetry

Volumn 15, Issue 8, 2004, Pages 1335-1341

  González Sabín, Javier ^a   Gotor, Vicente ^a   Rebolledo, Francisca ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 FORMYLPIPERAZIN 1 YL)CYCLOHEXANOL; 2 (4 METHOXYCARBONYLPIPERIDIN 1 YL)CYCLOHEXANOL; 2 (4 PHENYL 1,2,5,6 TETRAHYDROPYRIDIN 1 YL)CYCLOHEXANOL; 2 (4 PHENYLPIPERIDIN 1 YL)CYCLOHEXANOL; 2 (MORPHOLIN 4 YL)CYCLOHEXANOL; 2 (N BENZYL N METHYLAMINO)CYCLOHEXANOL; 2 (N ISOPROPYL N METHYLAMINO)CYCLOHEXANOL; 2 (PYRROLIDIN 1 YL)CYCLOHEXANOL; AMINE; AMINOALCOHOL; BENZALDEHYDE; CYCLOHEXANE OXIDE; CYCLOHEXANOL DERIVATIVE; DIETHYLZINC; ETHYLENE OXIDE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; VESAMICOL;

ADDITION REACTION; ARTICLE; BURKHOLDERIA CEPACIA; CATALYSIS; CATALYST; CHIRALITY; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ENZYME ISOLATION; PRIORITY JOURNAL; RACEMIZATION; TRANSESTERIFICATION;

EID: 1842737328     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.03.002     Document Type: Article

References (35)

1. Witiak D.T., Inbasekaran M.N. Grayson M. Kirk-Othmer Encycl. Chem. Technol. 17:1982;311-345.
2. Ager D.J., Prakash I., Schaad D.R. Chem. Rev. 96:1996;835-875.
3. Noyori R., Kitamura M. Angew. Chem., Int. Ed. Engl. 30:1991;34-48.
4. Tomioka K. Synthesis. 1990;541-549.
5. Coppola G.M., Schuster H.F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids. 1987;Wiley-Interscience, New York.
6. Abico A., Masamune S. Tetrahedron Lett. 33:1992;5517-5518.
7. Drauz K., Schwarm M., Mckennon M.J., Meyers A.I. J. Org. Chem. 58:1993;3568-3571.
8. Gontcharov A.V., Hong L., Sharpless K.B. Org. Lett. 1:1999;783-786.
9. O'Brien P. Angew. Chem., Int. Ed. 38:1999;326-329.
10. Reiser O. Angew. Chem., Int. Ed. Engl. 35:1996;1308-1309. and references cited therein.
11. Jacques J., Collet A., Wilen S.H. Enantiomers, Racemates and Resolutions. 1981;John Wiley, New York.
12. For some examples, see: Luna A., Astorga C., Fülop F., Gotor V. Tetrahedron: Asymmetry. 9:1998;4483-4487.
13. Sekar G., Kamble R.M., Singh V.K. Tetrahedron: Asymmetry. 10:1999;3663-3666.
14. Luna A., Maestro A., Astorga C., Gotor V. Tetrahedron: Asymmetry. 10:1999;1969-1977.
15. Clariana J., García-Granda S., Gotor V., Gutiérrez- Fernández A., Luna A., Moreno-Mañas M., Vallribera A. Tetrahedron: Asymmetry. 11:2000;4549-4557.
16. (a) Bain, A. I.; Beatch, G. N.; Longley, C. J.; Plouvier, B. M. C.; Sheng, T.; Walker, M. J. A.; Wall, R. A.; Yong, S. L.; Zhu, J.; Zolotoy, A. B. Patent 9 950 225, 1999; Chem. Abstr. 1999, 131, 257571
17. (b) MacLeod, B. A.; Walker, M. J. A.; Wall, R. A. U.S. Patent 5 637 583, 1997; Chem. Abstr. 1997, 127, 108837
18. Marshall I.G., Parsons S.M. Trends Neurosci. 10:1987;174-177.
19. Rogers G.A., Parsons S.M., Anderson D.C., Nilsson L.M., Bahr B.A., Kornreich W.D., Kaufman R., Jacobs R.S., Kirtman B. J. Med. Chem. 32:1989;1217-1230.
20. Wannan G., Prior C., Marshall I.G. Eur. J. Pharmacol. 201:1991;29-34.
21. Efange S.M.N., Mach R.H., Smith C.R., Khare A.B., Foulon C., Akella S.K., Childers S.R., Parsons S.M. Biochem. Pharmacol. 49:1995;791-797.
22. Fisher G.B., Goralski Ch.T., Nicholson L.W., Hasha D.L., Zakett D., Singaram B. J. Org. Chem. 60:1995;2026-2034.
23. Periasamy M., Kumar N.S., Sivakumar S., Rao V.D., Ramanathan C.R., Venkatraman L. J. Org. Chem. 66:2001;3828-3833.
24. Mousseron M., Jullien J., Jolchine Y. Bull. Soc. Chim. Fr. 19:1952;757-766.
25. García-Alles L.F., Gotor V. Biotechnol. Bioeng. 59:1998;684-694.
26. Chen C.S., Fujimoto Y., Girdaukas G., Sih C.J. J. Am. Chem. Soc. 104:1982;7294-7299.
27. Theil F. Tetrahedron. 56:2000;2905-2919.
28. Kazlauskas R.J., Weissfloch A.N.E., Rappaport A.T., Cuccia L.A. J. Org. Chem. 56:1991;2656-2665.
29. 1H NMR spectra were more complicated than that for (1S,2S)-2.
30. Seco J.M., Quiñoá E., Riguera R. Chem. Rev. 104:2004;17-117.
31. 3 group of (±)-2 to 2.42 (1S,2S) and 2.35 (1R,2R) ppm.
32. Dale J.A., Dull D.L., Mosher H.S. J. Org. Chem. 34:1969;2543-2549.
33. 3 as an external standard). For the MTPA-esters obtained from (1S,2S)-3 a major signal to - 72.19 was observed.
34. Sosa-Rivadeneyra M., Muñoz-Muñiz O., Anaya de Parrodi C., Quintero L., Juaristi E. J. Org. Chem. 68:2003;2369-2375.
35. D=+48 ( c 2.25, hexane).