Enzymatic Desymmetrising Redox Reactions for the Asymmetric Synthesis of Biaryl Atropisomers

Chemistry - A European Journal

Volumn 20, Issue 41, 2014, Pages 13084-13088

  Staniland, Samantha ^a   Yuan, Bo ^a   Giménez Agullõ, Nelson ^a   Marcelli, Tommaso ^b   Willies, Simon C ^a   Grainger, Damian M ^c   Turner, Nicholas J ^a   Clayden, Jonathan ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b POLITECNICO DI MILANO   (Italy)

^c JOHNSON MATTHEY TECHNOLOGY CENTRE   (United Kingdom)

Author keywords

atropisomerism; biaryls; biocatalysis; galactose oxidase; ketoreductase

Indexed keywords

DICHROISM;

ATROPISOMERISM; BIARYLS; BIOCATALYSIS; GALACTOSE OXIDASE; KETOREDUCTASE;

REDOX REACTIONS;

EID: 84941029578     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201404509     Document Type: Article

References (50)

1. A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, R. Noyori, J. Am. Chem. Soc. 1980, 102, 7932;
2. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
3. M. McCarthy, P. J. Guiry, Tetrahedron 2001, 57, 3809;
4. W. Tang, Z. Zhang, Chem. Rev. 2003, 103, 3029;
5. N. B. Johnson, I. C. Lennon, P. H. Moran, J. A. Ramsden, Acc. Chem. Res. 2007, 40, 1291.
6. P. Lloyd-Williams, E. Giralt, Chem. Soc. Rev. 2001, 30, 145;
7. M. C. Kozlowski, B. J. Morgan, E. C. Linton, Chem. Soc. Rev. 2009, 38, 3193;
8. J. Clayden, W. J. Moran, P. J. Edwards, S. R. LaPlante, Angew. Chem. 2009, 121, 6516;
9. Angew. Chem. Int. Ed. 2009, 48, 6398;
10. G. Bringmann, T. Gulder, T. A. M. Gulder, M. Breuning, Chem. Rev. 2011, 111, 563;
11. X. Fu, W. Fu, G. Liu, C. H. Senanayake, W. Tang, J. Am. Chem. Soc. 2014, 136, 8820.
12. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359;
13. G. Bringmann, A. J. PriceMortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5518;
14. Angew. Chem. Int. Ed. 2005, 44, 5384.
15. J. L. Gustafson, D. Lim, S. J. Miller, Science 2010, 328, 1251;
16. A. Bracegirdle, J. Clayden, L. W. Lai, Beilstein J. Org. Chem. 2008, 4, 47;
17. G. Bringmann, D. Menche, Acc. Chem. Res. 2001, 34, 615.
18. F. R. Leroux, A. Berthelot, L. Bonnafoux, A. Panossian, F. Colobert, Chem. Eur. J. 2012, 18, 14232;
19. J. Clayden, S. P. Fletcher, J. J. W. McDouall, S. J. M. Rowbottom, J. Am. Chem. Soc. 2009, 131, 5331;
20. J. Clayden, S. P. Fletcher, S. J. M. Rowbottom, M. Helliwell, Org. Lett. 2009, 11, 2313.
21. J. Clayden, P. M. Kubinski, F. Sammiceli, M. Helliwell, L. Diorazio, Tetrahedron 1994, 50, 4387;
22. J. Clayden, D. Mitjans, L. H. Youssef, J. Am. Chem. Soc. 2002, 124, 5266;
23. T. Thaler, F. Geittner, P. Knochel, Synlett 2007, 2655.
24. O. Baudoin, Eur. J. Org. Chem. 2005, 4223;
25. B. Lipshutz, F. Kayser, Z.-P. Liu, Angew. Chem. 1994, 106, 1962;
26. Angew. Chem. Int. Ed. Engl. 1994, 33, 1842;
27. A. N. Cammidge, K. V. L. Crépy, Chem. Commun. 2000, 1723;
28. J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12051;
29. Y. Zhou, S. Wang, W. Wu, Q. Li, Y. He, Y. Zhuang, L. Li, J. Pang, Z. Zhou, L. Qiu, Org. Lett. 2013, 15, 5508 and reference 2e).
30. E. García-Urdiales, I. Alfonso, V. Gotor, Chem. Rev. 2005, 105, 313;
31. T. Hudlicky, J. W. Reed, Chem. Soc. Rev. 2009, 38, 3117.
32. K. Okuyama, K. Shingubara, S. Tsujiyama, K. Suzuki, T. Matsumoto, Synlett 2009, 941;
33. T. Matsumoto, T. Konegawa, T. Nakamura, K. Suzuki, Synlett 2002, 122.
34. B. Yuan, A. Page, C. P. Worrall, F. Escalettes, S. C. Willies, J. J. W. McDouall, N. J. Turner, J. Clayden, Angew. Chem. 2010, 122, 7164;
35. Angew. Chem. Int. Ed. 2010, 49, 7010.
36. For an enzymatic resolution of a biaryl atropisomer, see
37. T. Taniguchi, T. A. Fukuba, S. Nakatsuka, S. Hayase, M. Kawatsura, H. Uno, T. Itoh, J. Org. Chem. 2008, 73, 3875. For non-enzymatic desymmetrisation of biaryl atropisomers, see
38. K. Mori, Y. Ichikawa, M. Kobayasji, Y. Shibata, M. Yamanaka, T. Akiyama, J. Am. Chem. Soc. 2013, 135, 3964;
39. T. Hayashi, S. Niizuma, T. Kamikawa, N. Suzuki, Y. Uozumi, J. Am. Chem. Soc. 1995, 117, 9101;
40. Q. Perron, A. Alexakis, Adv. Synth. Catal. 2010, 352, 2611. Note added in proof (August 21, 2014): After submission of this manuscript, a desymmetrising nitroxide-promoted oxidation was reported that leads to products similar to those described here: see
41. M. L. Lõpez, G. Royal, C. Philouze, P. Y. Chavant, V. Blandin, Eur. J. Org. Chem. 2014, 4884.
42. F. Escalettes, N. J. Turner, ChemBioChem 2008, 9, 857.
43. T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685.
44. S. I. Jeon, J. W. Hong, H. C. Yoon, Biotechnol. Lett. 2006, 28, 1401.
45. J. H. Carter, J. A. Deddens, J. L. Pullman, B. M. Colligan, L. O. Whiteley, H. W. Carter, Clin. Cancer Res. 1997, 3, 1479.
46. T. Butler, T. Schumacher, D. J. Namdjou, R. G. Gallego, H. Clausen, L. Elling, ChemBioChem 2001, 2, 884.
47. J. B. Rannes, A. Ioannou, S. C. Willies, G. Grogan, C. Behrens, S. L. Flitsch, N. J. Turner, J. Am. Chem. Soc. 2011, 133, 8436.
48. G. W. Huisman, J. Liang, A. Krebber, Curr. Opin. Chem. Biol. 2010, 14, 122.
49. M. D. Truppo, D. Pollard, P. Devine, Org. Lett. 2007, 9, 335.
50. B. R. Brooks, C. L. Brooks III, A. D. Mackerell, L. Nilsson, R. J. Petrella, B. Roux, Y. Won, G. Archontis, C. Bartels, S. Boresch, A. Caflisch, L. Caves, Q. Cui, A. R. Dinner, M. Feig, S. Fischer, J. Gao, M. Hodoscek, W. Im, K. Kuczera, T. Lazaridis, J. Ma, V. Ovchinnikov, E. Paci, R. W. Pastor, C. B. Post, J. Z. Pu, M. Schaefer, B. Tidor, R. M. Venable, H. L. Woodcock, X. Wu, W. Yang, D. M. York, M. Karplus, J. Comp. Chem. 2009, 30, 1545-1615.