Highly diastereo- and enantioselective tandem reaction toward functionalized pyrrolidines with multiple stereocenters

Organic Letters

Volumn 13, Issue 20, 2011, Pages 5596-5599

  Guo, Shengmei ^a   Xie, Yinjun ^a   Hu, Xinquan ^a,b   Huang, Hanmin ^a  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^b ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 80054705902     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2023196     Document Type: Article

References (39)

1. Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992.
2. Bunce, R. A. Tetrahedron 1995, 51, 13103
3. Tietze, L. F. Chem. Rev. 1996, 96, 115
4. Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551
5. Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001
6. Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1628
7. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134
8. Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570
9. Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354
10. Kitamura, M.; Miki, T.; Nakano, K.; Noyori, R. Tetrahedron Lett. 1996, 37, 5141
11. Feringa, B. L.; Pineschi, M. L.; Arnold, A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620
12. Keller, E.; Maurer, J.; Nassz, R.; Schader, T.; Meetsma, A.; Feringa, B. L. Tetrahedron: Asymmetry 1998, 9, 2409
13. Arnold, L. A.; Nassz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244
14. Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104
15. Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779
16. Rathgeb, X.; March, S.; Alexakis, A. J. Org. Chem. 2006, 71, 5737
17. Oliver, K.; Alexakis, A. Org. Lett. 2002, 4, 3835
18. Alexakis, A.; March, S. J. Org. Chem. 2002, 67, 8753
19. Agapiou, K.; Cauble, D. F.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4528
20. Li, K.; Alexakis, A. Tetrahedron Lett. 2005, 46, 5823
21. Li, K.; Alexakis, A. Chem.-Eur. J. 2007, 13, 3765
22. Xu, Y.-J.; Liu, Q.-Z.; Dong, L. Synlett 2007, 273
23. Howell, G. P.; Fletcher, S. P.; Geurts, K.; ter Horst, B.; Feringa, B. L. J. Am. Chem. Soc. 2006, 128, 14977
24. Arai, T.; Yokoyama, N. Angew. Chem., Int. Ed. 2008, 47, 4989
25. Anderson, J. C.; Stepney, G. J.; Mills, M. R.; Horsfall, L. R.; Blake, A. J.; Lewis, W. J. Org. Chem. 2011, 76, 1961
26. Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221
27. Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 1-110.
28. Heathcock, C. H. Modern Enolate Chemistry: Regio- and Stereoselective Formation of Enolates and the Consequence of Enolate Configuration on Subsequent Reactions; VCH: Weinheim, 1992.
29. Arya, P.; Qin, H. Tetrahedron 2000, 56, 917
30. Guo, S.; Xie, Y.; Hu, X.; Xia, C.; Huang, H. Angew. Chem., Int. Ed. 2010, 49, 2728
31. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
32. Larock, R. C. Comprehensive Organic Transformation; VCH, New York, 1989; p 411.
33. Hu, Y.; Liang, X.; Wang, J.; Zheng, Z.; Hu, X. J. Org. Chem. 2003, 68, 4542
34. For synthesis of and using this nitroalkene, see: Zhu, S.; Yu, S.; Wang, Y.; Ma, D. Angew. Chem., Int. Ed. 2010, 49, 4656
35. CCDC 834880 (3v), 834881 (3l), and 834882 (7a) contain 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/conts/ datarequest/cif.
36. Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1
37. Heathcock, C. H. In Comprehensive Carbanion Chemistry, Part B; Elsevier: Amsterdam, 1984; p 177.
38. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471
39. Pearson, W. H. In Studies in Natural Product Chemistry; Rahman, A. U., Ed.; Elsevier: New York, 1998; Vol. 1, p 323.