Enantioselective cyanoethoxycarbonylation of isatins promoted by a Lewis base-Brønsted acid cooperative catalyst

Angewandte Chemie - International Edition

Volumn 52, Issue 32, 2013, Pages 8299-8303

  Ogura, Yoshihiro ^a   Akakura, Matsujiro ^b,d   Sakakura, Akira ^c   Ishihara, Kazuaki ^a,d  

^a NAGOYA UNIVERSITY   (Japan)

^b AICHI UNIVERSITY OF EDUCATION   (Japan)

^c OKAYAMA UNIVERSITY   (Japan)

^d JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

asymmetric catalysis; Br nsted acids; isatins; Lewis bases; synthetic methods

Indexed keywords

ASYMMETRIC ACYLATION; ASYMMETRIC CATALYSIS; CYANOFORMATE; ENANTIOSELECTIVE; ISATINS; LEWIS BASIC SITE; LEWIS BASIS; SYNTHETIC METHODS;

CHEMICAL REACTIONS; CHEMISTRY;

CATALYSTS;

LEWIS ACID; LEWIS BASE;

ARTICLE; ASYMMETRIC CATALYSIS; BRØNSTED ACIDS; CATALYSIS; ISATINS; PHYSIOLOGY; PROTEIN CARBONYLATION; STEREOISOMERISM; SYNTHETIC METHODS;

ASYMMETRIC CATALYSIS; BRØNSTED ACIDS; ISATINS; LEWIS BASES; SYNTHETIC METHODS;

CATALYSIS; LEWIS ACIDS; LEWIS BASES; PROTEIN CARBONYLATION; STEREOISOMERISM;

EID: 84882241339     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201303572     Document Type: Article

References (69)

1. G. S. Singh, Z. Y. Desta, Chem. Rev. 2012, 112, 6104
2. N. Lashgari, G. M. Ziarani, Arkivoc 2012, 277
3. K. Shen, X. Liu, L. Lin, X. Feng, Chem. Sci. 2012, 3, 327
4. R. Dalpozzo, G. Bartoli, G. Bencivenni, Chem. Soc. Rev. 2012, 41, 7247
5. C. Marti, E. M. Carreira, Eur. J. Org. Chem. 2003, 2209
6. B. M. Trost, K. B. Brennan, Synthesis 2009, 3003.
7. L. Hong, R. Wang, Adv. Synth. Catal. 2013, 355, 1023
8. D. Wang, J. Liang, J. Feng, K. Wang, Q. Sun, L. Zhao, D. Li, W. Yan, R. Wang, Adv. Synth. Catal. 2013, 355, 548
9. Y.-L. Liu, J. Zhou, Chem. Commun. 2013, 49, 4421
10. A. A. Esmaeili, S. A. Ghalandarabad, M. Zangouei, Tetrahedron Lett. 2012, 53, 5605
11. N. V. Hanhan, N. R. Ball-Jones, N. T. Tran, A. K. Franz, Angew. Chem. 2012, 124, 1013
12. Angew. Chem. Int. Ed. 2012, 51, 989
13. L.-H. Sun, L.-T. Shen, S. Ye, Chem. Commun. 2011, 47, 10136
14. A. Sacchetti, A. Silvani, F. G. Gatti, G. Lesma, T. Pilati, B. Trucchi, Org. Biomol. Chem. 2011, 9, 5515
15. Y.-L. Liu, F. Zhou, J.-J. Cao, C.-B. Ji, M. Ding, J. Zhou, Org. Biomol. Chem. 2010, 8, 3847.
16. J. Wang, X. Liu, X. Feng, Chem. Rev. 2011, 111, 6947
17. S. Kobayashi, Y. Mori, J. S. Fossey, M. M. Salter, Chem. Rev. 2011, 111, 2626
18. J. Wang, W. T. Wang, W. Li, X. L. Hu, K. Shen, C. Tan, X. H. Liu, X. M. Feng, Chem. Eur. J. 2009, 15, 11642
19. M. North, D. L. Usanov, C. Young, Chem. Rev. 2008, 108, 5146
20. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713
21. H. Gröger, Chem. Rev. 2003, 103, 2795
22. S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069.
23. J. Gawronski, N. Wascinska, J. Gajewy, Chem. Rev. 2008, 108, 5227
24. N. H. Khan, R. I. Kureshy, S. H. R. Abdi, S. Agrawal, R. V. Jasra, Coord. Chem. Rev. 2008, 252, 593; and Ref. [3c-e].
25. N. H. Khan, S. Agrawal, R. I. Kureshy, S. H. R. Abdi, K. Pathak, H. C. Bajaj, Chirality 2010, 22, 153
26. N. H. Khan, S. Agrawal, R. I. Kureshy, S. H. R. Abdi, K. J. Prathap, R. V. Jasra, Eur. J. Org. Chem. 2008, 4511
27. Y. N. Belokon', W. Clegg, R. W. Harrington, E. Ishibashi, H. Nomura, M. North, Tetrahedron 2007, 63, 9724
28. S. Gou, X. Liu, X. Zhou, X. Feng, Tetrahedron 2007, 63, 7935
29. Y. N. Belokon', W. Clegg, R. W. Harrington, C. Young, M. North, Tetrahedron 2007, 63, 5287
30. W. Wang, S. Gou, X. Liu, X. Feng, Synlett 2007, 2875
31. S.-K. Chen, D. Peng, H. Zhou, L.-W. Wang, F.-X. Chen, X.-M. Feng, Eur. J. Org. Chem. 2007, 639
32. S. Gou, J. Wang, X. Liu, W. Wang, F.-X. Chen, X. Feng, Adv. Synth. Catal. 2007, 349, 343; and Ref. [3c].
33. S.-K. Tian, L. Deng, Tetrahedron 2006, 62, 11320
34. S.-K. Tian, L. Deng, J. Am. Chem. Soc. 2001, 123, 6195.
35. R. Chinchilla, C. Nájera, F. J. Ortega, A. Tarí, Tetrahedron: Asymmetry 2009, 20, 2279
36. R. Chinchilla, C. Nájera, F. J. Ortega, Tetrahedron: Asymmetry 2008, 19, 265
37. D. Peng, H. Zhou, X. Liu, L. Wang, S. Chen, X. Feng, Synlett 2007, 2448.
38. M. Shibasaki, M. Kanai, S. Matsunaga, N. Kumagai, Acc. Chem. Res. 2009, 42, 1117
39. K. Ishihara, Proc. Jpn. Acad. Ser. B 2009, 85, 290
40. K. Ishihara, A. Sakakura, M. Hatano, Synlett 2007, 686
41. H. Li, Y. Wang, L. Tang, L. Deng, J. Am. Chem. Soc. 2004, 126, 9906
42. M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491.
43. M.-X. Zhao, T.-L. Dai, R. Liu, D.-K. Wei, H. Zhou, F.-H. Ji, M. Shi, Org. Biomol. Chem. 2012, 10, 7970
44. W. Li, W. Wu, F. Yu, H. Huang, X. Liang, J. Ye, Org. Biomol. Chem. 2011, 9, 2505.
45. X.-F. Wang, Q.-L. Hua, Y. Cheng, X.-L. An, Q.-Q. Yang, J.-R. Chen, W.-J. Xiao, Angew. Chem. 2010, 122, 8557
46. Angew. Chem. Int. Ed. 2010, 49, 8379
47. C.-J. Wang, X.-Q. Dong, Z.-H. Zhang, Z.-Y. Xue, H.-L. Teng, J. Am. Chem. Soc. 2008, 130, 8606
48. C.-J. Wang, Z.-H. Zhang, X.-Q. Dong, X.-J. Wu, Chem. Commun. 2008, 44, 1431.
49. J.-S. Oh, J.-W. Lee, T. H. Ryu, J. H. Lee, C. E. Song, Org. Biomol. Chem. 2012, 10, 1052
50. H. B. Jang, H. S. Rho, J. S. Oh, E. H. Nam, S. E. Park, H. Y. Bae, C. E. Song, Org. Biomol. Chem. 2010, 8, 3918
51. W. Kaminsky, D. Responte, D. Daranciang, J. B. Gallegos, B.-C. Tran, T.-A. Pham, Molecules 2010, 15, 554
52. H. S. Rho, S. H. Oh, J. W. Lee, J. Y. Lee, J. Chin, C. E. Song, Chem. Commun. 2008, 1208
53. M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550
54. Angew. Chem. Int. Ed. 2006, 45, 1520.
55. CCDC 925315 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
56. W. Childs, S. G. Boxer, Biochemistry 2010, 49, 2725
57. P. A. Sigala, D. A. Kraut, J. M. M. Caaveiro, B. Pybus, E. A. Ruben, D. Ringe, G. A. Petsko, D. Herschlag, J. Am. Chem. Soc. 2008, 130, 13696
58. Y. Zhang, J. Kua, J. A. McCammon, J. Am. Chem. Soc. 2002, 124, 10572
59. A. K. Whiting, W. L. Peticolas, Biochemistry 1994, 33, 552.
60. E. V. Beletskiy, J. Schmidt, X.-B. Wang, S. R. Kass, J. Am. Chem. Soc. 2012, 134, 18534
61. M. B. Jiménez, V. Alcázar, R. Peláez, F. Sanz, Á. L. F. de Arriba, M. C. Caballero, Org. Biomol. Chem. 2012, 10, 1181
62. F. M. Muñiz, V. Alcázar, F. Sanz, L. Simón, Á. L. F. de Arriba, C. Raposo, J. R. Morán, Eur. J. Org. Chem. 2010, 6179
63. R. R. Knowles, E. N. Jacobsen, Proc. Natl. Acad. Sci. USA 2010, 107, 20678
64. M. Kotke, P. R. Schreiner, Synthesis 2007, 779
65. S. Kondo, T. Harada, R. Tanaka, M. Unno, Org. Lett. 2006, 8, 4621.
66. T. Könekamp, A. Ruiz, J. Duwenhorst, W. Schmidt, T. Borrmann, W.-D. Stohrer, F.-P. Montforts, Chem. Eur. J. 2007, 13, 6595
67. H. Ducatel, A. N. V. Nhien, D. Postel, Tetrahedron: Asymmetry 2008, 19, 67.
68. M. J. Frisch et al., Gaussian 03, Revision E.01, Gaussian, Inc., Wallingford, CT, 2004
69. M. J. Frisch et al., Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford, CT, 2009.