Fluxionally chiral DMAP catalysts: Kinetic resolution of axially chiral biaryl compounds

Angewandte Chemie - International Edition

Volumn 53, Issue 44, 2014, Pages 11818-11821

  Ma, Gaoyuan ^a   Deng, Jun ^a   Sibi, Mukund P ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

Acylation; Biaryls; Fluxionality; Kinetic resolution; Organocatalysis

Indexed keywords

ACYLATION; KINETICS; REACTION KINETICS;

4-DIMETHYLAMINOPYRIDINE; ASYMMETRIC TRANSFORMATIONS; BIARYLS; FLUXIONALITY; KINETIC RESOLUTION; ORGANOCATALYSIS; SECONDARY ALCOHOLS; SELECTIVITY FACTORS;

CATALYST SELECTIVITY;

EID: 84918816701     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201406684     Document Type: Article

References (51)

1. a) J. M. Keith, J. F. Larrow, E. N. Jacobsen, Adv. Synth. Catal. 2001, 343, 5;
2. E. Vedejs M. Jure Angew. Chem. 2005 117 4040
3. Angew. Chem. Int. Ed. 2005, 44, 3974;
4. C. E.Müller, P. R.Schreiner, Angew. Chem. 2011, 123, 6136;
5. Angew. Chem. Int. Ed. 2011, 50, 6012.
6. a) E. Vedejs, X. Chen, J. Am. Chem. Soc. 1996, 118, 1809;
7. b) T. Kawabata, M. Nagato, K. Takasu, K. Fuji, J. Am. Chem. Soc. 1997, 119, 3169;
8. c) J. C. Ruble, H. A. Latham, G. C. Fu, J. Am. Chem. Soc. 1997, 119, 1492;
9. d) A. C. Spivey, T. Fekner, S. E. Spey, H. Adams, J. Org. Chem. 1999, 64, 9430;
10. S.Arai, S.Bellemin-Laponnaz, G. C.Fu, Angew. Chem. 2001, 113, 240;
11. Angew. Chem. Int. Ed. 2001, 40, 234;
12. f) S. Yamada, T. Misono, Y. Iwai, A. Masumizu, Y. Akiyama, J. Org. Chem. 2006, 71, 6872;
13. C. ÓDálaigh, S. J. Connon, J. Org. Chem. 2007, 72, 7066;
14. h) R. P.Wurz, Chem. Rev. 2007, 107, 5570;
15. i) M. R. Crittall, H. S. Rzepa, D. R. Carbery, Org. Lett. 2011, 13, 1250;
16. j) E. Larionov, M. Mahesh, A. C. Spivey, Y. Wei, H. Zipse, J. Am. Chem. Soc. 2012, 134, 9390.
17. a) E. Vedejs, O. Daugulis, J. Am. Chem. Soc. 2003, 125, 4166;
18. b) G. T. Copeland, S. J. Miller, J. Am. Chem. Soc. 2001, 123, 6496;
19. c) V. B. Birman, E. W. Uffman, H. Jiang, X. Li, C. J. Kibane, J. Am. Chem. Soc. 2004, 126, 12226;
20. d) K. Ishihara, Y. Kosugi, M. Akakura, J. Am. Chem. Soc. 2004, 126, 12212;
21. e) T. Kano, K. Sasaki, K. Maruoka, Org. Lett. 2005, 7, 1347;
22. f) Y. Kawamata, T. Oriyama, Chem. Lett. 2010, 39, 382;
23. S.Harada, S.Kuwano, Y.Yamaoka, K.Yamada, K.Takasu, Angew. Chem. 2013, 125, 10417;
24. Angew. Chem. Int. Ed.2013, 52, 10227.
25. a) J. Chang, J. Reiner, J. Xie, Chem. Rev. 2005, 105, 4581;
26. b) M. C. Kozlowski, B. J. Morgan, E. C. Linton, Chem. Soc. Rev. 2009, 38, 3193;
27. c) G. Bringmann, T. Gulder, T. A. M. Gulder, M. Breuning, Chem. Rev. 2011, 111, 563.
28. a) R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345;
29. )W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029;
30. c) J.-H. Xie, Q.-L. Zhou, Acc. Chem. Res. 2008, 41, 581.
31. a) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999;
32. S. J.Connon, Angew. Chem. 2006, 118, 4013;
33. b) S. J. Connon, Angew. Chem. 2006, 118, 4013; Angew. Chem. Int. Ed. 2006, 45, 3909;
34. c) Y. Chen, S. Yekta, A. K. Yudin, Chem. Rev. 2003, 103, 3155;
35. d) Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su, Chem. Rev. 2005, 105, 1603;
36. e) M. Shibasaki, S. Matsunaga, Chem. Soc. Rev. 2006, 35, 269;
37. f) M. Rueping, A. Kuenkel, I. Atodiresei, Chem. Soc. Rev. 2011, 40, 4539.
38. a) H. Aoyama, M. Tokunaga, J. Kiyosu, T. Iwasawa, Y. Obora, Y. Tsuji, J. Am. Chem. Soc. 2005, 127, 10474; for kinetic resolution with biaryl-derived catalysts, see:
39. b) K. Mori, Y. Ichikawa, M. Kobayashi, Y. Shibata, M. Yamanaka, T. Akiyama, J. Am. Chem. Soc. 2013, 135, 3964;
40. S. Shirakawa X. Wu K. Maruoka Angew. Chem. 2013 125 14450
41. c) S. Shirakawa, X. Wu, K. Maruoka, Angew. Chem. 2013, 125, 14450; Angew. Chem. Int. Ed. 2013, 52, 14200;
42. D.-J. Cheng, L. Yan, S.-K. Tian, M.-Y. Wu, L.-X. Wang, Z.-L. Fan, S.-C. Zheng, X.-Y. Liu, B. Tan, Angew. Chem. 2014, 126, 3758;
43. Angew. Chem. Int. Ed. 2014, 53, 3684.
44. S. Arseniyadis, M. Mahesh, P. McDaid, T. Hampel, S. G. Davey, A. C. Spivey, Collect. Czech. Chem. Commun. 2011, 76, 1239.
45. a) M. P. Sibi, L. Venkatraman, M. Liu, C. P. Jasperse, J. Am. Chem. Soc. 2001, 123, 8444;
46. b) M. P. Sibi, R. Zhang, S. Manyem, J. Am. Chem. Soc. 2003, 125, 9306;
47. c) M. P. Sibi, S. Manyem, H. Palencia, J. Am. Chem. Soc. 2006, 128, 13660;
48. d) M. P. Sibi, L. M. Stanley, X. Nie, L. Venkatraman, M. Liu, C. P. Jasperse, J. Am. Chem. Soc. 2007, 129, 395;
49. e) M. P. Sibi, K. Kawashima, L. Stanley, Org. Lett. 2009, 11, 3894.
50. V. B. Birman, L. Guo, Org. Lett. 2006, 8, 4859.
51. J. M. Brunel, Chem. Rev. 2005, 105, 857.