Palladium-catalyzed dynamic kinetic asymmetric transformation of racemic biaryls: Axial-to-central chirality transfer

Journal of the American Chemical Society

Volumn 137, Issue 15, 2015, Pages 4876-4879

  Yang, Liu ^a   Zheng, Huayu ^a   Luo, Lei ^a   Nan, Jiang ^a   Liu, Jingjing ^a   Wang, Yaoyu ^a   Luan, Xinjun ^a  

^a NORTHWEST UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY; PALLADIUM COMPOUNDS;

BIARYLS; CHIRALITY TRANSFER; DYNAMIC KINETIC ASYMMETRIC TRANSFORMATIONS; INTERNAL ALKYNES; PALLADIUM-CATALYZED; QUATERNARY STEREOCENTERS; SPIROCYCLIC PRODUCTS;

KINETICS;

2' BROMO [1,1' BIPHENYL] 4 OLS; 4 (2 BROMOARYL)NAPHTHALEN 1 OLS; ALKYNE; BIARYL; BIPHENYL DERIVATIVE; CARBON; FUNCTIONAL GROUP; NAPHTHALENE DERIVATIVE; PALLADIUM; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DYNAMIC KINETIC ASYMMETRIC TRANSFORMATION; ENANTIOMER; ENANTIOSELECTIVITY; RACEMIC MIXTURE; SPIROANNULATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84928501353     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b01285     Document Type: Article

References (61)

1. Trost, B. M.; Fandrick, D. R. Aldrichimica Acta 2007, 40, 59
2. Steinreiber, J.; Faber, K.; Griengl, H. Chem.-Eur. J. 2008, 14, 8060
3. Huerta, F. F.; Minidis, A. B. E.; Bäckvall, J. E. Chem. Soc. Rev. 2001, 30, 321
4. Rachwalski, M.; Vermue, N.; Rutjes, F. P. J. T. Chem. Soc. Rev. 2013, 42, 9268
5. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 3543
6. Trost, B. M.; McEachern, E. J. J. Am. Chem. Soc. 1999, 121, 8649
7. Edin, M.; Steinreiber, J.; Bäckvall, J. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5761
8. Parsons, A. T.; Johnson, J. S. J. Am. Chem. Soc. 2009, 131, 3122
9. Yamaguchi, A.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 10842
10. Wang, Y.; Kuzniewski, C. N.; Rauniyar, V.; Hoong, C.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 12972
11. Dornan, P. K.; Kou, K. G. M.; Houk, K. N.; Dong, V. M. J. Am. Chem. Soc. 2014, 136, 291
12. de Nanteuil, F.; Serrano, E.; Perrotta, D.; Waser, J. J. Am. Chem. Soc. 2014, 136, 6239
13. Mikami, K.; Yoshida, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 858
14. Zhao, Y.; Tam, Y.; Wang, Y.; Li, Z.; Sun, J. Org. Lett. 2012, 14, 1398
15. Wang, Y.; Zhang, W.; Ma, S. J. Am. Chem. Soc. 2013, 135, 11517
16. Imada, Y.; Ueno, K.; Kutsuwa, K.; Murahashi, S. Chem. Lett. 2002, 140
17. Trost, B. M.; Fandrick, D. R.; Dinh, D. J. Am. Chem. Soc. 2005, 127, 14186
18. Deska, J.; del Pozo Ochoa, C.; Bäckvall, J. E. Chem.-Eur. J. 2010, 16, 4447
19. Wan, B.; Ma, S. Angew. Chem., Int. Ed. 2013, 52, 441
20. Zhang, Z.; Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2007, 129, 14148
21. Osborne, J. D.; Randell-Sly, H. E.; Currie, G. S.; Cowley, A. R.; Willis, M. C. J. Am. Chem. Soc. 2008, 130, 17232
22. Chen, M.; Roush, W. R. J. Am. Chem. Soc. 2011, 133, 5744
23. Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed. 2013, 52, 10630
24. Clayden, J.; Lai, L. W. Angew. Chem., Int. Ed. 1999, 38, 2556
25. Chan, V.; Kim, J. G.; Jimeno, C.; Carroll, P. J.; Walsh, P. J. Org. Lett. 2004, 6, 2051
26. Barrett, K. T.; Miller, S. J. J. Am. Chem. Soc. 2013, 135, 2963
27. Bringmann, G.; Breuning, M.; Henschel, P.; Hinrichs, J. Org. Synth. 2002, 79, 72
28. Ashizawa, T.; Tanaka, S.; Yamada, T. Org. Lett. 2008, 10, 2521
29. Gustafson, J. L.; Lim, D.; Miller, S. J. Science 2010, 328, 1251
30. Ros, A.; Estepa, B.; Ramírez-López, P.; álvarez, E.; Fernández, R.; Lassaletta, J. M. J. Am. Chem. Soc. 2013, 135, 15730
31. Bhat, V.; Wang, S.; Stoltz, B. M.; Virgil, S. C. J. Am. Chem. Soc. 2013, 135, 16829
32. Campolo, D.; Gastaldi, S.; Roussel, C.; Bertrand, M. P.; Nechab, M. Chem. Soc. Rev. 2013, 42, 8434
33. De Jong, F.; Siegel, M. G.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1975, 551
34. Baker, R. W.; Kyasnoor, R. V.; Sargent, M. V.; Shelton, B. W.; White, A. H. Aust. J. Chem. 2000, 53, 487
35. Yasui, Y.; Suzuki, K.; Matsumoto, T. Synlett 2004, 619
36. Nan, J.; Zuo, Z.; Luo, L.; Bai, L.; Zheng, H.; Yuan, Y.; Liu, J.; Luan, X.; Wang, Y. J. Am. Chem. Soc. 2013, 135, 17306
37. Gu, S.; Luo, L.; Liu, J.; Bai, L.; Zheng, H.; Wang, Y.; Luan, X. Org. Lett. 2014, 16, 6132
38. Zheng, H.; Bai, L.; Liu, J.; Nan, J.; Zuo, Z.; Yang, L.; Wang, Y.; Luan, X. Chem. Commun. 2015, 51, 3061
39. Zuo, Z.; Yang, X.; Liu, J.; Nan, J.; Bai, L.; Wang, Y.; Luan, X. J. Org. Chem. 2015, 80, 3349
40. Roche, S. P.; Porco, J. A., Jr Angew. Chem., Int. Ed. 2011, 50, 4068
41. Zhuo, C.; Zhang, W.; You, S. Angew. Chem., Int. Ed. 2012, 51, 12662
42. Nemoto, T.; Ishige, Y.; Yoshida, M.; Kohno, Y.; Kanematsu, M.; Hamada, Y. Org. Lett. 2010, 12, 5020
43. Uyanik, M.; Yasui, T.; Ishihara, H. Angew. Chem., Int. Ed. 2010, 49, 2175
44. Wu, Q.; Liu, W.; Zhuo, C.; Rong, Z.; Ye, K.; You, S. Angew. Chem., Int. Ed. 2011, 50, 4455
45. Rousseaux, S.; García-Fortanet, J.; Del Aguila Sanchez, M. A.; Buchwald, S. J. Am. Chem. Soc. 2011, 133, 9282
46. Oguma, T.; Katsuki, T. J. Am. Chem. Soc. 2012, 134, 20017
47. Zhuo, C.; You, S. Angew. Chem., Int. Ed. 2013, 52, 10056
48. Dohi, T.; Takenaga, N.; Nakae, T.; Toyoda, Y.; Yamasaki, M.; Shiro, M.; Fujioka, H.; Maruzama, A.; Kita, Y. J. Am. Chem. Soc. 2013, 135, 4558
49. Phipps, R. J.; Toste, F. D. J. Am. Chem. Soc. 2013, 135, 1268
50. Wang, S.; Yin, Q.; Zhuo, C.; You, S. Angew. Chem., Int. Ed. 2015, 54, 647
51. Nan, J.; Liu, J.; Zheng, H.; Zuo, Z.; Hou, L.; Hu, H.; Wang, Y.; Luan, X. Angew. Chem., Int. Ed. 2015, 54, 2356
52. Yang, D.; Wang, L.; Han, F.; Li, D.; Zhao, D.; Wang, R. Angew. Chem., Int. Ed. 2015, 54, 2185
53. Lafon, O.; Lesot, P.; Fan, C.; Kagan, H. B. Chem.-Eur. J. 2007, 13, 3772
54. Bott, G.; Field, L. D.; Sternhell, S. J. Am. Chem. Soc. 1980, 102, 5618
55. Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225
56. Funk, T. W.; Berlin, J. M.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 1840
57. Chaulagain, M. R.; Sormunen, G. J.; Montgomery, J. J. Am. Chem. Soc. 2007, 129, 9568
58. Lee, K.; Hoveyda, A. H. J. Org. Chem. 2009, 74, 4455
59. Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402
60. Jensen, D. R.; Sigman, M. S. Org. Lett. 2003, 5, 63
61. Xu, L.; Shi, Y. J. Org. Chem. 2008, 73, 749