Simple branched sulfur-olefins as chiral ligands for Rh-catalyzed asymmetric arylation of cyclic ketimines: Highly enantioselective construction of tetrasubstituted carbon stereocenters

Journal of the American Chemical Society

Volumn 135, Issue 3, 2013, Pages 971-974

  Wang, Hui ^a   Jiang, Tao ^a   Xu, Ming Hua ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; ASYMMETRIC ADDITION; CARBON STEREOCENTERS; CHIRAL LIGAND; ENANTIOSELECTIVE; ENANTIOSELECTIVE CONSTRUCTION; KETIMINES; OLEFIN LIGANDS; QUATERNARY CARBON;

BIOCHEMISTRY; CATALYSIS; ENANTIOSELECTIVITY; OLEFINS; RHODIUM; SULFUR;

LIGANDS;

ALKENE; BASE; CARBON; IMINE; LIGAND; RHODIUM; SOLVENT; SULFINAMIDE; SULFUR;

ARTICLE; ARYLATION; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; REACTION OPTIMIZATION; SCREENING; STEREOCHEMISTRY;

ALKENES; AMIDES; CARBON; CATALYSIS; IMINES; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRILES; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM; SULFUR;

EID: 84872785966     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3110818     Document Type: Article

References (75)

1. Baker, D. C.; Jiang, B. U.S. Patent 6,353,112 B1, 2002.
2. Mao, J.; Baker, D. C. U.S. Patent 6,458,962 B1, 2003.
3. Yoakim, C.; O'Meara, J.; Simoneau, B.; Ogilvie, W. W.; Deziel, R. Patent Appl. WO 2004026875 A1, 2004.
4. Jirgensons, A.; Leitis, G.; Kalvinsh, I.; Robinson, D.; Finn, P.; Khan, N. Patent Appl. WO 2008142376 A1, 2008.
5. Reiser, O. In Organic Synthesis Highlights IV; Schmalz, H.-G., Ed.; Wiley-VCH: Weinheim, Germany, 2000; p 11.
6. Oppolzer, W.; Wills, M.; Starkemann, C.; Bernardinelli, G. Tetrahedron Lett. 1990, 31, 4117
7. Oppolzer, W.; Wills, M.; Kelly, M. J.; Signer, M.; Blagg, J. Tetrahedron Lett. 1990, 31, 5015
8. Davis, F. A.; Chen, B.-C. Chem. Rev. 1992, 92, 919
9. Differding, E.; Lang, R. W. Tetrahedron Lett. 1991, 32, 1779
10. Takeuchi, Y.; Suzuki, T.; Satoh, A.; Shiragami, T.; Shibata, N. J. Org. Chem. 1999, 64, 5708
11. Liu, Z.; Shibata, N.; Takeuchi, Y. J. Org. Chem. 2000, 65, 7583
12. Kim, B. H.; Curran, D. P. Tetrahedron 1993, 49, 293
13. Brodsky, B. H.; Du Bois, J. J. Am. Chem. Soc. 2005, 127, 15391
14. Majumdar, K. C.; Mondal, S. Chem. Rev. 2011, 111, 7749
15. Meléndez, R. E.; Lubell, W. D. Tetrahedron 2003, 59, 2581
16. Ahn, K. H.; Baek, H.-H.; Lee, S. J.; Cho, C.-W. J. Org. Chem. 2000, 65, 7690
17. Liu, Z.; Shibata, N.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. 1 2002, 302
18. Lee, J.; Zhong, Y. L.; Reamer, R. A.; Askin, D. Org. Lett. 2003, 5, 4175
19. Nicolaou, K. C.; Snyder, S. A.; Longbottom, D. A.; Nalbandian, A. Z.; Huang, X. Chem.-Eur. J. 2004, 10, 5581
20. Penso, M.; Albanese, D.; Landini, D.; Lupi, V.; Tagliabue, A. J. Org. Chem. 2008, 73, 6686
21. Hopkins, M. J.; Hanson, P. R. Org. Lett. 2008, 10, 2223
22. Chen, X.-Y.; Lin, R.-C.; Ye, S. Chem. Commun. 2012, 48, 1317
23. Rassadin, V. A.; Grosheva, D. S.; Arefeva, I. A.; Tomashevskiy, A. A.; Sokolov, V. V.; de Meijere, A. Eur. J. Org. Chem. 2012, 5028
24. Rommel, M.; Fukuzumi, T.; Bode, J. W. J. Am. Chem. Soc. 2008, 130, 17266
25. Enders, D.; Seppelt, M. Synlett 2011, 402
26. Trost, B. M.; Silverman, S. M. J. Am. Chem. Soc. 2012, 134, 4941
27. Luo, Y.-F.; Hepburn, H. B.; Chotsaeng, N.; Lam, H. W. Angew. Chem., Int. Ed. 2012, 51, 8309
28. Ahn, K. H.; Ham, C.; Kim, S.-K.; Cho, C.-W. J. Org. Chem. 1997, 62, 7047
29. Yang, Q.; Shang, G.; Gao, W.; Deng, J.; Zhang, X. Angew. Chem., Int. Ed. 2006, 45, 3832
30. Yu, C.-B.; Wang, D.-W.; Zhou, Y.-G. J. Org. Chem. 2009, 74, 5633
31. Wang, Y.-Q.; Yu, C.-B.; Wang, D.-W.; Wang, X.-B.; Zhou, Y.-G. Org. Lett. 2008, 10, 2071
32. Chen, F.; Li, Z.; He, Y.; Fan, Q. Chin. J. Chem. 2010, 28, 1529
33. Ichinose, M.; Suematsu, H.; Yasutomi, Y.; Nishioka, Y.; Uchida, T.; Katsuki, T. Angew. Chem., Int. Ed. 2011, 50, 9884
34. Berger, R.; Duff, K.; Leighton, J. L. J. Am. Chem. Soc. 2004, 126, 5686
35. Lauzon, C.; Charette, A. Org. Lett. 2006, 8, 2743
36. Wada, R.; Shibuguchi, T.; Makino, S.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7687
37. Fu, P.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 5530
38. Shintani, R.; Takeda, M.; Tsuji, T.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 13168
39. Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853
40. Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626
41. Nishimura, T.; Noishiki, A.; Tsui, G. C.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 5056
42. Luo, Y.-F.; Carnell, A. J.; Lam, H. W. Angew. Chem., Int. Ed. 2012, 51, 6762
43. Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364
44. Johnson, J. B.; Rovis, T. Angew. Chem., Int. Ed. 2008, 47, 4482
45. Defieber, C.; Grützmacher, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4482
46. Shintani, R.; Hayashi, T. Aldrichimica Acta 2009, 42, 31
47. Feng, C.-G.; Xu, M.-H.; Lin, G.-Q. Synlett 2011, 1345
48. Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508
49. Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628
50. Maire, P.; Deblon, S.; Breher, F.; Geier, J.; Böhler, C.; Rüegger, H.; Schönberg, H.; Grützmacher, H. Chem.-Eur. J. 2004, 10, 4198
51. Shintani, R.; Duan, W.-L.; Nagano, T.; Okada, A.; Hayashi, T. Angew. Chem., Int. Ed. 2005, 44, 4611
52. Defieber, C.; Ariger, M. A.; Moriel, P.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 3139
53. Roggen, M.; Carreira, E. M. J. Am. Chem. Soc. 2010, 132, 11917
54. Schafroth, M. A.; Sarlah, D.; Krautwald, S.; Carreira, E. M. J. Am. Chem. Soc. 2012, 134, 20276
55. Lafrance, M.; Roggen, M.; Carreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 3470
56. Hahn, B. T.; Tewes, F.; Fröhlich, R.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 1143
57. Jin, S.-S.; Wang, H.; Xu, M.-H. Chem. Commun. 2011, 47, 7230
58. Qi, W.-Y.; Zhu, T.-S.; Xu, M.-H. Org. Lett. 2011, 13, 3410
59. Jin, S.-S.; Wang, H.; Zhu, T.-S.; Xu, M.-H. Org. Biomol. Chem. 2012, 10, 1764
60. Zhu, T.-S.; Jin, S.-S.; Xu, M.-H. Angew. Chem., Int. Ed. 2012, 51, 780
61. Wang, H.; Zhu, T.-S.; Xu, M.-H. Org. Biomol. Chem. 2012, 10, 9158
62. Zhu, T.-S.; Chen, J.-P.; Xu, M.-H. Chem.-Eur. J. 2013, 19, 865
63. Thaler, T.; Guo, L.-N.; Steib, A. K.; Raducan, M.; Karaghiosoff, K.; Mayer, P.; Knochel, P. Org. Lett. 2011, 13, 3182
64. Feng, X.; Wang, Y.; Wei, B.; Yang, J.; Du, H. Org. Lett. 2011, 13, 3300
65. Chen, G.; Gui, J.; Li, L.; Liao, J. Angew. Chem., Int. Ed. 2011, 50, 7681
66. Xue, F.; Li, X.; Wan, B. J. Org. Chem. 2011, 76, 7256
67. Khiar, N.; Salvador, A.; Chelouan, A.; Alcudia, A.; Fernández, I. Org. Biomol. Chem. 2012, 10, 2366
68. Zhu, T.-S.; Xu, M.-H. Chem. Commun. 2012, 48, 7274 and references cited therein
69. Asymmetric Fluoroorganic Chemistry: Synthesis, Application and Future Directions; Ramachandran, P. V., Ed.; American Chemical Society: Washington, DC, 2000.
70. Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508
71. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169
72. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829
73. Kantchev, E. A. B. Chem. Commun. 2011, 47, 10969
74. Gosiewska, S.; Raskatov, J. A.; Shintani, R.; Hayashi, T.; Brown, J. M. Chem.-Eur. J. 2012, 18, 80
75. Luo, Y.; Berry, N. G.; Carnell, A. J. Chem. Commun. 2012, 48, 3279