Recent advances in organocatalytic asymmetric synthesis of polysubstituted pyrrolidines

Tetrahedron Letters

Volumn 55, Issue 4, 2014, Pages 784-794

  Han, Man Yi ^a   Jia, Ju Ying ^a   Wang, Wei ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Asymmetric synthesis; Organocatalysis; Substituted pyrrolidine

Indexed keywords

ALKENE; AMINE; BRONSTED ACID; NITROOLEFIN DERIVATIVE; PYRROLIDINE DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG; AZOMETHINE YLIDE; HYDROGEN;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; MICHAEL ADDITION; ONE POT SYNTHESIS; ORGANOCATALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; AMINATION; CATALYST; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; ELECTRON; ENANTIOSELECTIVITY; HORNER REACTION; HYDROGEN BOND; MANNICH REACTION; ORGANOCATALYTIC ASYMMETRIC SYNTHESIS;

EID: 84892437576     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.11.048     Document Type: Review

References (60)

1. For selected reviews, see: V. Nair, and T.D. Suja Tetrahedron 63 2007 12247
2. S. Hanessian ChemMedChem 1 2006 1300
3. S.G. Pyne, and M.-Y. Tang Curr. Org. Chem. 9 2005 1393
4. J.R. Liddell Nat. Prod. Rep. 19 2002 773
5. F.J. Sardina, and H. Rapoport Chem. Rev. 96 1996 1825
6. W.H. Pearson Atta-Ur-Rahman Studies in Natural Product Chemistry 1998 Elsevier New York 323 Vol. 1
7. For selected reviews, see: S. Mukherjee, J.W. Yang, S. Hoffmann, and B. List Chem. Rev. 107 2007 5471
8. A. Erkkilä, I. Majander, and P.M. Pihko Chem. Rev. 107 2007 5416
9. A. Berkessel, and H. Gröger Asymmetric Organocatalysis 2005 Wiley-VCH Weinheim
10. For selected reviews, see: D.W.C. MacMillan Nature 455 2008 304
11. J.T. Mohr, M.R. Krout, and B.M. Stoltz Nature 455 2008 323
12. B. List Chem. Rev. 107 2007 5413
13. B. List, and J.W. Yang Science 313 2006 1584
14. P.I. Dalko, and L. Moisan Angew. Chem., Int. Ed. 43 2004 5138
15. K.N. Houk, and B. List Acc. Chem. Res. 37 2004 487
16. For selected reviews, see: J. Yu, F. Shi, and L.-Z. Gong Acc. Chem. Res. 44 2011 1156
17. S. Pandey K Tetrahedron: Asymmetry 2 2011 1817
18. X. Companyó, A.-N. Alba, and R. Rios Targets Heterocycl. Syst. 13 2009 147
19. J. Vicario, D. Badia, L. Carrillo, N. Ruiz, and E. Reyes Targets Heterocycl. Syst. 12 2008 302
20. G. Pandey, P. Banerjee, and S.R. Gadre Chem. Rev. 106 2006 4484
21. J.L. Vicario, S. Reboredo, D. Badía, and L. Carrillo Angew. Chem., Int. Ed. 46 2007 5168
22. A. Iza, L. Carrillo, J.L. Vicario, D. Badía, E. Reyes, and J.I. Martínez Org. Biomol. Chem. 8 2010 2238
23. S. Reboredo, E. Reyes, J.L. Vicario, D. Badía, L. Carrillo, A. de Cózar, and F.P. Cossío Chem. Eur. J. 18 2012 7179
24. S. Reboredo, J.L. Vicario, D. Badía, L. Carrillo, and E. Reyes Adv. Synth. Catal. 353 2011 3307
25. S. Lin, L. Deiana, G.-L. Zhao, J. Sun, and A. Córdova Angew. Chem., Int. Ed. 50 2011 7624
26. C. Wang, X.-H. Chen, S.-M. Zhou, and L.-Z. Gong Chem. Commun. 2010 1275
27. N. Li, J. Song, X.-F. Tu, B. Liu, X.-H. Chen, and L.-Z. Gong Org. Biomol. Chem. 8 2010 2016
28. M.-N. Cheng, H. Wang, and L.-Z. Gong Org. Lett. 13 2011 2418
29. L. He, X.-H. Chen, D.-N. Wang, S.-W. Luo, W.-Q. Zhang, J. Yu, L. Ren, and L.-Z. Gong J. Am. Chem. Soc. 133 2011 13504
30. F. Shi, Z.-L. Tao, S.-W. Luo, S.-J. Tu, and L.-Z. Gong Chem. Eur. J. 18 2012 6885
31. C. Guo, J. Song, and L.-Z. Gong Org. Lett. 15 2013 2676
32. J.-F. Bai, L.-L. Wang, L. Peng, Y.-L. Guo, J.-N. Ming, F.-Y. Wang, X.-Y. Xu, and L.-X. Wang Eur. J. Org. Chem. 23 2011 4472
33. L.-L. Wang, J.-F. Bai, L. Peng, L.-W. Qi, L.-N. Jia, Y.-L. Guo, X.-Y. Luo, X.-Y. Xu, and L.-X. Wang Chem. Commun. 2012 5175
34. L. Wang, X.-M. Shi, W.-P. Dong, L.-P. Zhu, and R. Wang Chem. Commun. 2013 3458
35. T.D. Beeson, A. Mastracchio, J.B. Hong, K. Ashton, and D.W.C. MacMillan Science 316 2007 582
36. N.T. Jui, J.A.O. Garber, F.G. Finelli, and D.W.C. MacMillan J. Am. Chem. Soc. 134 2012 11400
37. N. Ono The Nitro Group in Organic Synthesis 2001 Wiley-VCH NewYork
38. S. Zhu, S. Yu, Y. Wang, and D. Ma Angew. Chem., Int. Ed. 49 2010 4656
39. J. Chen, Z.-C. Geng, N. Li, X.-F. Huang, F.-F. Pan, and X.-W. Wang J. Org. Chem. 78 2013 2362
40. K. Xu, S. Zhang, Y. Hu, Z. Zha, and Z. Wang Chem. Eur. J. 19 2013 3573
41. C. Wang, X. Yang, G. Raabe, and D. Enders Adv. Synth. Catal. 354 2012 2629
42. B. Zheng, H. Wang, Y. Han, C. Liu, and Y. Peng Chem. Commun. 2013 4561
43. J. Duschmalé, and H. Wennemers Chem. Eur. J. 18 2012 1111
44. L. Wang, X. Zhang, and D. Ma Tetrahedron 68 2012 7675
45. H. Ma, K. Liu, F.-G. Zhang, C.-L. Zhu, J. Nie, and J.-A. Ma J. Org. Chem. 75 2010 1402
46. M.-Y. Han, Y. Zhang, H.-Z. Wang, W.-K. An, B.-C. Ma, Y. Zhang, and W. Wang Adv. Synth. Catal. 354 2012 2635
47. M.-Y. Han, H.-Z. Wang, W.-K. An, J.-Y. Jia, B.-C. Ma, Y. Zhang, and W. Wang Chem. Eur. J. 19 2013 8078
48. T. Ma, X. Fu, C.W. Kee, L. Zong, Y. Pan, K.-W. Huang, and C.-H. Tan J. Am. Chem. Soc. 133 2011 2828
49. S. Shirakawa, Y. Liu, A. Usui, and K. Maruoka ChemCatChem 4 2012 980
50. S. Sternativo, O. Walczak, B. Battistelli, L. Testaferri, and F. Marini Tetrahedron 68 2012 10536
51. C. Grondal, M. Jeanty, and D. Enders Nat. Chem. 2 2010 167
52. D. Enders, C. Grondal, and M.R.M. Hüttl Angew. Chem., Int. Ed. 46 2007 1570
53. B. List Chem. Commun. 2006 819
54. J.-Y. Bae, H.-J. Lee, S.-H. Youn, S.-H. Kwon, and C.-W. Cho Org. Lett. 12 2010 4352
55. P. Breistein, J. Johansson, I. Ibrahem, S. Lin, L. Deiana, J. Sun, and A. Córdova Adv. Synth. Catal. 354 2012 1156
56. I. Kumar, N.A. Mir, V.K. Gupta, and Rajnikant Chem. Commun. 2012 6975
57. T. Cheng, S. Meng, and Y. Huang Org. Lett. 15 2013 1958
58. D. Enders, D.P. Göddertz, C. Beceño, and G. Raabe Adv. Synth. Catal. 352 2010 2863
59. A. Jean, J. Blanchet, J. Rouden, J. Maddaluno, and M. De Paolis Chem. Commun. 2013 1651
60. J. Chen, L. Zhou, and Y.-Y. Yeung Org. Biomol. Chem. 10 2012 3808