Stereoselective chemoenzymatic synthesis of enantiopure 1-(Heteroaryl)ethanamines by lipase-Catalysed kinetic resolutions

European Journal of Organic Chemistry

Volumn , Issue 15, 2009, Pages 2533-2538

  Alatorre Santamaria, Sergio ^a   Gotor Fernandez, Vicente ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Amines; Chirality; Enzyme catalysis; Heterocycles; Kinetic resolution

Indexed keywords

EID: 66149107074     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900150     Document Type: Article

References (25)

1. a) H. Y. Lo, J. Bentzien, R. W. Fleck, S. S. Pullen, H. H. Khine, J. WoskaJr., S. Z. Kugler, M. A. Kashem, H. Takahashi, Chem. Lett. 2008, 18, 6218-6221;
2. b) H. Y. Lo, J. Bentzien, A. White, C. C. Man, R. W. Fleck, S. S. Pullen, H. H. Khine, J. King, J. Woska Jr., J. P. Wolak, M. A. Kashem, G. P. Roth, H. Takahashi, Tetrahedron Lett. 2008, 49, 7337-7340.
3. H. Lopez-Sandoval, M. E. Londono-Lemos, R. Garza-Velasco, I. Poblano-Melendez, P. Granada-Macfas, I. Gracia-Mora, N. Barba-Behrens, J. Inorg. Chem. 2008, 102, 1267-1276.
4. B. Machura, R. Kruszynski, J. Kusz, Polyhedron 2008, 27, 1679-1689.
5. V. Gotor, I. Alfonso, E. Garcfa-Urdiales (Ed.), Asymmetric Organic Synthesis with Enzymes, Wiley-VCH, Weinheim, Germany, 2008.
6. a) J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337-2347;
7. b) N. Ran, L. Zhao, Z. Chen, J. Tao, Green Chem. 2008,10, 361-372;
8. c) J. M. Woodley, Trends Biotechnol. 2008, 26, 321-327.
9. a) U. T. Bornscheuer, R. J. Kazlauskas (Eds.), Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations, 2nd ed., Wiley-VCH, Weinheim, Germany, 2005;
10. b) V. Gotor-Fernandez, R. Brieva, V. Gotor, J. Mol. Catal. B: Enzym. 2006, 40, 111-120.
11. a) L. E. Iglesias, V. M. Sanchez, F. Rebolledo, V. Gotor, Tetrahedron: Asymmetry 1997, 8, 2675-2677;
12. b) K. A. Skupinska, E. J. McEachern, I. R. Baird, R. T. Skerlj, G. J. Bridger, J. Org. Chem. 2003, 68, 3546-3551;
13. c) A. E. Sigmund, R. DiCosimo, Tetrahedron: Asymmetry 2004, 15, 2797-2799;
14. d) O. Torre, E. Busto, V. Gotor-Fernandez, V. Gotor, Adv. Synth. Catal. 2007, 349, 1481-1488;
15. e) J. B. Crawford, R. T. Skerlj, G. J. Bridger, J. Org. Chem. 2007, 72, 669-671;
16. f) K. Ditrich, Synthesis 2008, 2283-2287.
17. See for example: a) C. Paizs, M. To§a, V. Bodai, G. Szakacs, I. Kmecz, B. Simandi, C. Madjik, L. Novak, F.-D. Irimie, L. Poppe, Tetrahedron: Asymmetry 2003, 14, 1943-1949;
18. b) R. K. Cheedral, R. Sachwani, R. Krishna, Tetrahedron: Asymmetry 2008, 19, 901-905;
19. c) M. To?a, S. Pilbak, M. Moldovan, C. Paizs, G. Szatzker, G. Szakacs,L.Novak, F.-D. Irimie, L. Poppe, Tetrahedron: Asymmetry 2008, 19, 1844-1852;
20. d) M. I. To§a, P. V. Podea, C. Paizs, F.-D. Irimie, Tetrahedron: Asymmetry 2008, 19, 2068-2071.
21. M. J. Tebbe, W. A. Spitzer, F. Victor, S. C. Miller, C. C. Lee, T. R. Sattelberg, E. McKinney, C. J. Tang, J. Med. Chem. 1997, 40, 3937-3946.
22. H. Skolnik, J. G. Miller, A. R. Day, J. Am. Chem. Soc. 1943, 65, 1854-1858.
23. E. Zang, C. Chow, Chin. Chem. Lett. 1991, 2, 169-170.
24. a) V. Gotor-Fernandez, V. Gotor, Curr. Org. Chem. 2006, 10, 1125-1143;
25. b) V. Gotor-Fernandez, E. Busto, V. Gotor, Adv. Synth. Catal. 2006, 348, 797-812.