Enantioselective synthesis of axially chiral biaryl monophosphine oxides via direct asymmetric suzuki coupling and DFT investigations of the enantioselectivity

ACS Catalysis

Volumn 4, Issue 5, 2014, Pages 1390-1397

  Zhou, Yougui ^a   Zhang, Xuepeng ^a   Liang, Huiyi ^a   Cao, Zhenkun ^a   Zhao, Xiaoyu ^a   He, Yuwei ^a   Wang, Shouliang ^a   Pang, Jiyan ^a   Zhou, Zhongyuan ^b   Ke, Zhuofeng ^a   Qiu, Liqin ^a,c  

^a SUN YAT SEN UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

asymmetric catalysis; biaryls; computational chemistry; phosphine oxides; Suzuki coupling

Indexed keywords

COMPUTATIONAL CHEMISTRY; HYDROGEN BONDS; PALLADIUM COMPOUNDS; PHOSPHORUS COMPOUNDS;

ASYMMETRIC CATALYSIS; BIARYLS; ENANTIOSELECTIVE SYNTHESIS; HIGH ENANTIOSELECTIVITY; METAL HYDROGEN BONDS; PHOSPHINE OXIDE; REDUCTIVE ELIMINATION; SUZUKI COUPLINGS;

ENANTIOSELECTIVITY;

EID: 84899808509     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs500208n     Document Type: Article

References (38)

1. Hayashi, T. Acc. Chem. Res. 2000, 33, 354-362
2. Hayashi, T. Catal. Today 2000, 62, 3-15
3. Gibson, S. E.; Rudd, M. Adv. Synth. Catal. 2007, 349, 781-795
4. Hargaden, G. C.; Guiry, P. J. Chem. Rev. 2009, 109, 2505-2550
5. Hamada, T.; Chieffi, A.; Åhman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268
6. RajanBabu, T. V.; Nomura, N.; Jin, J.; Nandi, M.; Park, H.; Sun, X. J. Org. Chem. 2003, 68, 8431-8446
7. Kawashima, Y.; Okano, K.; Nozaki, K.; Hiyama, T. Bull. Chem. Soc. Jpn. 2004, 77, 347-355
8. Xie, X.; Zhang, T. Y.; Zhang, Z. J. Org. Chem. 2006, 71, 6522-6529
9. Han, J. W.; Hayashi, T. Tetrahedron: Asymmetry 2010, 21, 2193-2197
10. Huang, Z.; Liu, Z.; Zhou, J. J. Am. Chem. Soc. 2011, 133, 15882-15885
11. Li, Q.; Wan, P.; Wang, S.; Zhuang, Y.; Li, L.; Zhou, Y.; He, Y.; Cao, R.; Qiu, L.; Zhou, Z. Appl. Catal., A 2013, 458, 201-206
12. Uozumi, Y.; Suzuki, N.; Ogiwara, A.; Hayashi, T. Tetrahedron 1994, 50, 4293-4302
13. Ding, K.; Wang, Y.; Yun, H.; Liu, J.; Wu, Y.; Terada, M.; Okubo, Y.; Mikami, K. Chem.-Eur. J. 1999, 5, 1734-1737
14. Wang, Y.; Guo, H.; Ding, K. Tetrahedron: Asymmetry 2000, 11, 4153-4162
15. Luo, Y.; Wang, F.; Zhu, G.; Zhang, Z. Tetrahedron: Asymmetry 2004, 15, 17-19
16. Hoshi, T.; Hayakawa, T.; Suzuki, T.; Hagiwara, H. J. Org. Chem. 2005, 70, 9085-9087
17. Hoshi, T.; Sasaki, K.; Sato, S.; Ishii, Y.; Suzuki, T.; Hagiwara, H. Org. Lett. 2011, 13, 932-935
18. Cammidge, A. N.; Crépy, K. V. L. Chem. Commun. 2000, 18, 1723-1724
19. Genov, M.; Almorín, A.; Espinet, P. Chem.-Eur. J. 2006, 12, 9346-9352
20. Bermejo, A.; Ros, A.; Fernández, R.; Lassaletta, J. M. J. Am. Chem. Soc. 2008, 130, 15798-15799
21. Uozumi, Y.; Matsuura, Y.; Arakawa, T.; Yamada, Y. M. A. Angew. Chem., Int. Ed. 2009, 48, 2078-2710
22. Shen, X.; Jones, G. O.; Watson, D. A.; Bhayana, B.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 11278-11287
23. Yamamoto, T.; Akai, Y.; Nagata, Y.; Suginome, M. Angew. Chem., Int. Ed. 2011, 50, 8844-8847
24. Wu, W.; Wang, S.; Zhou, Y.; He, Y.; Zhuang, Y.; Li, L.; Wan, P.; Wang, L.; Zhou, Z.; Qiu, L. Adv. Synth. Catal. 2012, 354, 2395-2402
25. Lundin, P. M.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 11027-11029
26. Wilsily, A.; Tramutola, F.; Owston, N. A.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 5794-5797
27. Tang, W.; Patel, N. D.; Xu, G.; Xu, X.; Savoie, J.; Ma, S.; Hao, M.-H.; Keshipeddy, S.; Capacci, A. G.; Wei, X.; Zhang, Y.; Gao, J. J.; Li, W.; Rodriguez, S.; Lu, B. Z.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2012, 14, 2258-2261
28. Zhang, S.-S.; Wang, Z.-Q.; Xu, M.-H.; Lin, G.-Q. Org. Lett. 2010, 12, 5546-5549
29. Ros, A.; Estepa, B.; Bermejo, A.; álvarez, E.; Fernández, R.; Lassaletta, J. M. J. Org. Chem. 2012, 77, 4740-4750
30. Xu, G.; Fu, W.; Liu, G.; Senanayake, C. H.; Tang, W. J. Am. Chem. Soc. 2014, 136, 570-573
31. Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051-12052
32. Wang, S.; Li, J.; Miao, T.; Wu, W.; Li, Q.; Zhuang, Y.; Zhou, Z.; Qiu, L. Org. Lett. 2012, 14, 1966-1969
33. Zhou, Y.; Wang, S.; Wu, W.; Li, Q.; He, Y.; Zhuang, Y.; Li, L.; Pang, J.; Zhou, Z.; Qiu, L. Org. Lett. 2013, 15, 5508-5511
34. Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 24, 1461-1473
35. Ogasawara, M.; Yoshida, K.; Kamei, H.; Kato, K.; Uozumi, Y.; Hayshi, T. Tetrahedron: Asymmetry 1998, 9, 1779-1787
36. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
37. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
38. Joncour, A.; Decor, A.; Liu, J. M.; Dau, M.; Baudoin, O. Chem.-Eur. J. 2007, 13, 5450-5465