An enantioselective tandem reduction/nitro-Mannich reaction of nitroalkenes using a simple thiourea organocatalyst

Chemical Science

Volumn 4, Issue 7, 2013, Pages 2897-2901

  Anderson, James C ^a   Koovits, Paul J ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CATALYSTS; ASYMMETRIC SYNTHESIS; CATALYTIC TRANSFORMATION; DIASTEREOMERIC RATIOS; EFFICIENT SYNTHESIS; NITRO-MANNICH REACTION; NITROGEN-CONTAINING MOLECULES; TRIFLUOROACETAMIDES;

CHEMICAL REACTIONS; ENANTIOSELECTIVITY; THIOUREAS;

CATALYSTS;

EID: 84878798474     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc50613d     Document Type: Article

References (52)

1. V. Khama, S. Ranganathan, BMC Bioinformatics, 2009, 10, S10
2. D. O'Hagan, Modern Alkaloids: Structure, Isolation, Synthesis and Biology, Wiley-VCH, Weinheim, Germany, 2007
3. J. P. Michael, Nat. Prod. Rep., 2008, 25, 139
4. R. Ballini, M. Petrini, Tetrahedron, 2004, 60, 1017
5. C. Palomo, M. Oiarbibe, R. Halder, A. Laso, R. López, Angew. Chem., Int. Ed., 2006, 45, 117
6. L. Bernadi, B. F. Bonini, I. E. Capito, G. Dessole, M. Comes-Franchimi, M. Fochi, A. Ricci, J. Org. Chem., 2004, 69, 8168
7. H. Adams, J. C. Anderson, S. Peace, A. M. K. Pennel, J. Org. Chem., 1998, 63, 9932
8. D. H. Lloyd, D. E. Nichols, J. Org. Chem., 1986, 51, 4294
9. A. G. M. Barrett, C. D. Spilling, Tetrahedron Lett., 1988, 29, 5733
10. M. A. Sturgess, D. J. Yarberry, Tetrahedron Lett., 1993, 34, 4743
11. M. G. Bursavich, D. H. Rich, J. Med. Chem., 2002, 45, 541
12. P. Jakubec, D. M. Cockfield, D. Dixon, J. Am. Chem. Soc., 2009, 131, 16632
13. P. Jakubec, A. F. Kyle, J. Calleja, D. J. Dixon, Tetrahedron Lett., 2011, 52, 6094
14. A. F. Kyle, P. Jakubec, D. M. Cockfield, E. Cleator, J. Skidmore, D. J. Dixon, Chem. Commun., 2011, 47, 10037
15. B. Shen, J. N. Johnston, Org. Lett., 2008, 10, 4397
16. G. Kumaraswarmy, A. Pitchaiah, Helv. Chim. Acta, 2011, 94, 1543
17. P. Jakubec, A. Hawkins, W. Felzmann, D. J. Dixon, J. Am. Chem. Soc., 2012, 134, 17482
18. N. Tsuritani, K.-I. Yamada, N. Yoshikawa, M. Shibasaki, Chem. Lett., 2002, 276
19. X. Xu, T. Furukawa, T. Okino, H. Miyabe, Y. Takemoto, Chem.-Eur. J., 2006, 12, 466
20. P. S. Hynes, P. A. Stupple, D. J. Dixon, Org. Lett., 2008, 10, 1389
21. K. L. Jensen, P. H. Poulsen, B. S. Donslund, F. Morana, K. A. Jørgensen, Org. Lett., 2012, 14, 1516
22. S. Handa, V. Gnanadesikan, S. Matsunga, M. J. Shibasaki, J. Am. Chem. Soc., 2010, 132, 4925
23. J. Weng, Y.-B. Li, R.-B. Wang, F.-Q. Li, C. Liu, A. S. C. Chan, G. Lu, J. Org. Chem., 2010, 75, 3125
24. G. Kumaraswarmy, A. Pitchaiah, Tetrahedron, 2011, 67, 2536
25. T. A. Davis, J. N. Johnston, Chem. Sci., 2011, 2, 1076
26. T. A. Davis, M. W. Danneman, J. N. Johnston, Chem. Commun., 2012, 48, 5578
27. H. Xie, Y. Zhang, S. Zhang, X. Chen, W. Wang, Angew. Chem., Int. Ed., 2011, 50, 11773
28. E. Marquéz-López, P. Merino, T. Tejero, R. P. Herrera, Eur. J. Org. Chem., 2009, 2401
29. A. Noble, J. C. Anderson, Chem. Rev., 2013, 113, 2887
30. T. A. Davis, J. C. Wilt, J. N. Johnston, J. Am. Chem. Soc., 2010, 132, 2880
31. W. Huang, C. Peng, L. Guo, R. Hu, B. Han, Synlett, 2011, 2981
32. R. A. Shenvi, D. P. O'Malley, P. S. Barran, Acc. Chem. Res., 2009, 42, 530
33. L. F. Tietze, Chem. Rev., 1996, 96, 115
34. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem., Int. Ed., 2006, 45, 7134
35. I. Ibrahem, A. Córdova, Angew. Chem., Int. Ed., 2006, 45, 1952
36. S. Mukherjee, B. List, J. Am. Chem. Soc., 2007, 129, 11336
37. C. J. Chapman, C. G. Frost, Synthesis, 2007, 1
38. A. M. Walji, D. W. C. MacMillan, Synlett, 2007, 1477
39. Z.-Y. Han, H. Xiao, X.-H. Chenand, L.-Z. Gong, J. Am. Chem. Soc., 2009, 131, 9182
40. H. Jiang, P. Elsner, K. L. Jensen, A. Falcicchio, V. Marcos, K. A. Jørgensen, Angew. Chem., Int. Ed., 2009, 48, 6844
41. S. Belot, K. A. Vogt, C. Besnard, N. Krause, A. Alexakis, Angew. Chem., Int. Ed., 2009, 48, 8923
42. J. C. Anderson, A. J. Blake, P. J. Koovits, G. J. Stepney, J. Org. Chem., 2012, 77, 4711
43. C. Wang, X. Dong, Z. Zhang, Z. Xue, H. Teng, J. Am. Chem. Soc., 2008, 130, 8606
44. S. Handa, V. Gnanadesikan, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc., 2010, 132, 4925
45. T. Okino, S. Nakamura, T. Furukawa, Y. Takemoto, Org. Lett., 2004, 6, 625
46. T. P. Yoon, E. N. Jacobsen, Angew. Chem., Int. Ed., 2005, 44, 466
47. X. Xu, T. Furukawa, T. Okino, H. Miyabe, Y. Takemoto, Chem.-Eur. J., 2006, 12, 466
48. N. J. A. Martin, L. Ozores, B. List, J. Am. Chem. Soc., 2007, 129, 8976
49. S. G. Ouellet, A. Walji, D. W. C. Macmillan, Acc. Chem. Res., 2007, 40, 1327
50. T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc., 2003, 125, 12672
51. S. J. Zuend, E. N. Jacobsen, J. Am. Chem. Soc., 2009, 131, 15358
52. J. C. Anderson, G. J. Stepney, M. R. Mills, L. R. Horsfall, A. J. Blake, W. Lewis, J. Org. Chem., 2011, 76, 1961