Biocatalytic desymmetrization of an atropisomer with both an enantioselective oxidase and ketoreductases

Angewandte Chemie - International Edition

Volumn 49, Issue 39, 2010, Pages 7010-7013

  Yuan, Bo ^a   Page, Abigail ^a   Worrall, Christopher P ^a   Escalettes, Franck ^a   Willies, Simon C ^a   McDouall, Joseph J W ^a   Turner, Nicholas J ^a   Clayden, Jonathan ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Asymmetric synthesis atropisomerism biocatalysis diaryl ethers enzymes

Indexed keywords

ATROPISOMERISM; ATROPISOMERS; BENZYLIC; DESYM-METRIZATION; DIARYL ETHERS; ENANTIOSELECTIVE; ENZYMATIC OXIDATIONS; GALACTOSE OXIDASE; HYDROXY GROUPS; KETOREDUCTASES;

ALDEHYDES; CATALYSTS; ENZYMES; ISOMERS;

ETHERS;

ETHER DERIVATIVE; GALACTOSE OXIDASE; OXIDOREDUCTASE;

ARTICLE; BIOCATALYSIS; CHEMISTRY; COMPUTER SIMULATION; ENZYME ACTIVE SITE; METABOLISM; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

BIOCATALYSIS; CATALYTIC DOMAIN; COMPUTER SIMULATION; ETHERS; GALACTOSE OXIDASE; OXIDATION-REDUCTION; OXIDOREDUCTASES; STEREOISOMERISM;

EID: 77956914045     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002580     Document Type: Article

References (56)

1. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994
2. Y.-M. Li, F.-Y. Kwong, W.-Y. Yu, A. S. C. Chan, Coord. Chem. Rev. 2007, 251, 2119;
3. M. Berthod, G. Mignani, G. Woodward, M. Lemaire, Chem. Rev. 2005, 105, 1801.
4. R. Noyori, Angew. Chem. 2002, 114, 2108.
5. Angew. Chem. Int. Ed. 2002, 41, 2008.
6. binap = 2, 2'-bis(diphenylphosphanyl)-1, 1'- binaphthyl.
7. (a) G. Bringmann, A. J. P. Mortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5518;
8. Angew. Chem. Int. Ed. 2005, 44, 5384
9. (b) A. N. Cammidge, K. V. L. Crepy, Chem. Commun. 2000, 1723
10. J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051.
11. T. Itoh, J. Org. Chem. 1995, 60, 4968
12. O. Kitagawa, M. Fujita, M. Kohriya, H. Hasegawa, T. Taguchi, Tetrahedron Lett. 2000, 41, 8539
13. T. Watanabe, K. Kamikawa, M. Uemura, Tetrahedron Lett. 1995, 36, 6695
14. R. Rios, C. Jimeno, P.J. Carroll, P. J. Walsh, J. Am. Chem. Soc. 2002, 124, 10272
15. J. Clayden, H. Turner, Tetrahedron Lett. 2009, 50, 3216
16. D. Pamperin, H. Hopf, C. Syldatk, M. Pietzsch, Tetrahedron: Asymmetry 1997, 8, 319
17. D. Pamperin, C. Schulz, H. Hopf, C. Syldatk, M. Pietzsch, Eur. J. Org. Chem. 1998, 1441.
18. (a) G. Bringmann, R.-M. Pfeifer, P. Schreiber, K. Hartner, M. Schraut, M. Breuning, Tetrahedron 2004, 60, 4349
19. G. Bring-mann, D. Menche, Acc. Chem. Res. 2001, 34, 615
20. G. Bringmann, J. Hinrichs, T. Pabst, P. Henschel, K. Peters, E.-M. Peters, Synthesis 2001, 155
21. A. Bracegirdle, J. Clayden, L. W. Lai, Beilstein J. Org. Chem. 2008, 4, 47
22. (b) J. Clayden, P. Johnson, J. H. Pink, M. Helliwell, J. Org. Chem. 2000, 65, 7033
23. J. Clayden, D. Mitjans, L. H. Youssef, J. Am. Chem. Soc. 2002, 124, 5266
24. J. Clayden, L. W. Lai, M. Helliwell, Tetrahedron 2004, 60, 4399
25. J. Clayden, C. P. Worrall, W. Moran, M. Helliwell, Angew. Chem. 2008, 120, 3278
26. Angew. Chem. Int. Ed. 2008, 47, 3234
27. J. Clayden, J. Senior, M. Helliwell, Angew. Chem. 2009, 121, 6388
28. Angew. Chem. Int. Ed. 2009, 48, 6270
29. J. Clayden, S. P. Fletcher, J. J. W. McDouall, S. J. M. Rowbottom, J. Am. Chem. Soc. 2009, 131, 5331.
30. (a) E. García-Urdiales, I. Alfonso, V. Gotor, Chem. Rev. 2005, 105, 313
31. (b) L. M. Engelhardt, W.-P. Leung, C. L. Raston, G. Salem, P. Twiss, A. H. White, J. Chem. Soc. Dalton Trans. 1988, 2403
32. (c) T. Hayashi, S. Niizuma, T. Kamikawa, N. Suzuki, Y. Uozumi, J. Am. Chem. Soc. 1995, 117, 9101
33. T. Kamikawa, Y. Uozumi, T. Hayashi, Tetrahedron Lett. 1996, 37, 3161
34. (d) T. M. T. Tuyet, T. Harada, K. Hashimoto, M. Hatsuta, A. Oku, J. Org. Chem. 2000, 65, 1335
35. T. Harada, T. M. T. Tuyet, A. Oku, Org. Lett. 2000, 2, 1319
36. e) T. Matsumoto, T. Konegawa, T. Nakamura, K. Suzuki, Synlett 2002, 122.
37. F. Escalettes, N.J. Turner, ChemBioChem 2008, 9, 857-860
38. M. D. Truppo, F. Escalettes, N. J. Turner, Angew. Chem. 2008, 120, 2679-2681
39. Angew. Chem. Int. Ed. 2008, 47, 2639-2641.
40. G. W. Huisman, J. Liang, A. Krebber, Curr. Opin. Chem. Biol. 2010, 14, 122-129.
41. M. S. Betson, J. Clayden, C. P. Worrall, S. Peace, Angew. Chem. 2006, 118, 5935
42. Angew. Chem. Int. Ed. 2006, 45, 5803.
43. K. C. Nicolaou, C. N. C. Boddy, S. Brase, N. Winssinger, Angew. Chem 1999, 111, 2230
44. Angew Chem Int Ed 1999, 38, 2096.
45. For uses of non-biaryl atropisomers in catalysis
46. For uses of non-biaryl atropisomers in catalysis, see: A. Honda, K. M. Waltz, P. J. Carroll, P. J. Walsh, Chirality 2003, 15, 615
47. W.- M. Dai, K. K. Y. Yeing, J.-T. Liu, Y. Zhang, I. D. Williams, Org. Lett. 2002, 4, 1615
48. W.-M. Dai, K. K. Y. Yeung, Y. Wang, Tetrahedron 2004, 60, 4425
49. W.-M. Dai, Y. Li, Y. Zhang, Z. Yue, J. H. Wu, Chem. Eur. J. 2008, 14, 5538
50. S. Brandes, B. Niess, M. Bella, A. Prieto, J. Overgaard, K. A. Jørgensen, Chem. Eur. J. 2006, 12, 6039.
51. W. Kroutil, A. Kleewein, K. Faber, Tetrahedron: Asymmetry 1997, 8, 3263-3274.
52. Attempted kinetic resolution with GOase of a less hindered compound with an isopropyl group in place of the tert-butyl group gave the racemic compound, probably as a result of racemization on the timescale of the reaction: compound 2 is resolvable by HPLC, but related compounds have low barriers to racemization (see Ref. ).
53. See: A. Ahmed, R. A. Bragg, J. Clayden, L. W. Lai, C. McCarthy, J. H. Pink, N. Westlund, S. A. Yasin, Tetrahedron 1998, 54, 13277.
54. S. J. Firbank, M. S. Rogers, C. M. Wilmot, D. M. Dooley, M. A. Halcrow, P. F. Knowles, M. J. McPherson, S. E. Phillips, Proc. Natl. Acad. Sci. USA 2001, 98, 12932.
55. M. D. Truppo, D. Pollard, P. Devine, Org. Lett. 2007, 9, 335-338.
56. All ketoreductases (KREDs) were obtained from Codexis Inc., 200 Penobscot Drive, Redwood City, CA 94063, USA.