Highly enantioselective Rh-catalyzed transfer hydrogenation of N-sulfonyl ketimines

Tetrahedron Asymmetry

Volumn 21, Issue 7, 2010, Pages 800-804

  Kwak, Se Hun ^a,b   Lee, Sun Ah ^a   Lee, Kee In ^a,b  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b University of Science and Technology (UST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ENAMINE; FORMIC ACID; IMINE; OXIME; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM; SULFONE DERIVATIVE; TRIETHYLAMINE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS;

EID: 77956494600     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.04.047     Document Type: Article

References (39)

1. For reviews, see: (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97;
2. (b) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045;
3. (c) Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226;
4. (d) Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393.
5. Farina, V.; Reeves, J. T.; Senanayake, C. H.; Song, J. J. Chem. Rev. 2006, 106, 2734.
6. (a) Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916;
7. (b) Mao, Z.; Baker, D. C. Org. Lett. 1999, 1, 841;
8. (c) Ahn, K. H.; Ham, C.; Kim, S.-K.; Cho, C. W. J. Org. Chem. 1997, 62, 7047;
9. (d) Wu, J.; Wang, F.; Ma, Y.; Cui, X.; Cun, L.; Zhu, J.; Deng, J.; Yu, B. Chem. Commun. 2006, 1766.
10. (a) Wang, Y.-Q.; Lu, S.-M.; Zhou, Y.-G. J. Org. Chem. 2007, 72, 3729;
11. (b) Yang, Q.; Shang, G.; Gao, W.; Deng, J.; Zhang, X. Angew. Chem., Int. Ed. 2006, 45, 3832.
12. Baker, A. J.; Martin, J. In Asymmetric Catalysis on Industrial Scale; Blaser, H.-U., Schmidt, E., Eds.; Wiley-VCH, 2004; p 201.
13. (a) Nishikori, H.; Yoshihara, R.; Hosomi, A. Synlett 2003, 561;
14. (b) Charette, A. B.; Giroux, A. Tetrahedron Lett. 1996, 37, 6669.
15. (a) Lee, D.-M.; Lee, J.-C.; Jeong, N.; Lee, K.-I. Tetrahedron: Asymmetry 2007, 18, 2662;
16. (b) Lee, D.-M.; Kumaraswamy, G.; Lee, K.-I. Monatsh. Chem. 2009, 140, 73;
17. (c) Lee, D.-M.; Kwak, S. H.; Lee, K.-I. Bull. Korean Chem. Soc. 2009, 30, 1317;
18. (d) Kwak, S. H.; Lee, D.-M.; Lee, K.-I. Tetrahedron: Asymmetry 2009, 20, 2639.
19. (a) Cavalli, A.; Bolognesi, M. L.; Minarini, A.; Rosini, M.; Tumiatti, V.; Recanatini, M.; Melchiorre, C. J. Med. Chem. 2008, 51, 347;
20. (b) Jones, T. K.; Mohan, J. J.; Xavier, L. C.; Blacklock, T. J.; Mathre, D. J.; Sohar, P.; Jones, E. T. T.; Reamer, R. A.; Roberta, F. E.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 763;
21. (c) Bosiak, M. J.; Krzemiński, M. P.; Jaisankar, P.; Zaidlewicz, M. Tetrahedron: Asymmetry 2008, 19, 956;
22. (d) Siddiqui, S. A.; Srinivasan, K. V. Tetrahedron: Asymmetry 2007, 18, 2099.
23. (a) Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc. 1991, 113, 1713;
24. (b) Huang, X.; Huang, J.; Wen, Y.; Feng, X. Adv. Synth. Catal. 2006, 348, 2579;
25. (c) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1992, 57, 4777;
26. (d) Artman, D. D., III; Bartolozzi, A.; Franck, R. W.; Weinreb, S. M. Synlett 2001, 232.
27. Ruano, J. L. G.; Alemán, J.; Cid, M. B.; Parra, A. Org. Lett. 2005, 7, 179.
28. Sano, T.; Horiguchi, Y.; Toda, J.; Imafuku, K.; Tsuda, Y. Chem. Pharm. Bull. 1984, 32, 497.
29. (a) Kurihara, K.; Yamamoto, Y.; Miyaura, N. Adv. Synth. Catal. 2009, 351, 260;
30. (b) Ngai, M.-Y.; Barchuk, A.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12644;
31. (c) Wang, J.; Hu, X.; Jiang, J.; Gou, S.; Hwang, X.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2007, 46, 8468.
32. Guijarro, D.; Pablo, Ó.; Yus, M. Tetrahedron Lett. 2009, 50, 5386.
33. (a) Mashima, K.; Abe, T.; Tani, K. Chem. Lett. 1998, 1199;
34. (b) Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186.
35. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.
36. (a) Wagner, K. Angew. Chem., Int. Ed. 1970, 9, 50;
37. (b) Narita, K.; Sekiya, M. Chem. Pharm. Bull. 1977, 25, 135.
38. Nishimura, T.; Yasuhara, Y.; Hayashi, T. Org. Lett. 2006, 8, 979.
39. Leverett, C. A.; Cassidy, M. P.; Padwa, A. J. Org. Chem. 2006, 71, 8591.