Using conveniently designed α-amino ketones in Michael reactions under iminium catalysis: Enantioselective synthesis of γ-lactams and γ-amino-δ-keto esters

Advanced Synthesis and Catalysis

Volumn 355, Issue 4, 2013, Pages 653-658

  Talavera, Garazi ^a   Reyes, Efraím ^a   Vicario, Jose L ^a   Carrillo, Luisa ^a   Uria, Uxue ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

asymmetric catalysis; heterocycles; Michael reaction; organocatalysis; pyrrolidines

Indexed keywords

EID: 84874719634     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200987     Document Type: Article

References (45)

1. Catalytic Asymmetric Conjugate Reactions, (Ed.:, A. Cordova,), Wiley-VCH, Weinheim, 2010
2. Comprehensive Asymmetric Catalysis, Vol. 3, (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer-Verlag, Berlin, 1999; for some reviews, see
3. H.-C. Guo, J.-A. Ma, Angew. Chem. 2006, 118, 362
4. Angew. Chem. Int. Ed. 2006, 45, 354
5. T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829
6. A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221
7. N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171
8. M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033
9. J. Leonard, E. Díez-Barra, S. Merino, Eur. J. Org. Chem. 1998, 2051
10. N. Krause, Angew. Chem. 1998, 110, 295
11. Angew. Chem. Int. Ed. 1998, 37, 283
12. B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771.
13. D. W. C. MacMillan, Nature 2008, 455, 304
14. E. N. Jacobsen, D. W. C. MacMillan, Proc. Natl. Acad. Sci. USA 2010, 107, 20618
15. C. F. Barbas II, Angew. Chem. 2008, 120, 44
16. Angew. Chem. Int. Ed. 2008, 47, 42
17. A. Dondoni, M. Massi, Angew. Chem. 2008, 120, 4716
18. Angew. Chem. Int. Ed. 2008, 47, 4638
19. Chem. Rev. 2007, 107, No. 12, special issue on organocatalysis
20. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232
21. Angew. Chem. Int. Ed. 2008, 47, 6138
22. B. List, Chem. Commun. 2006, 819
23. M. J. Gaunt, C. C. Johansson, Chem. Rev. 2007, 107, 5596
24. P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248
25. Angew. Chem. Int. Ed. 2004, 43, 5138
26. S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178.
27. A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416
28. G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79.
29. J. L. Vicario, D. Badia, L. Carrillo, Synthesis 2007, 2065
30. D. Almaçi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 299
31. S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701.
32. D. A. Alonso, S. Kitagaki, N. Utsumi, C. F. Barbas III, Angew. Chem. 2008, 120, 4664
33. Angew. Chem. Int. Ed. 2008, 47, 4588.
34. a values, see: http://www.chem.wisc.edu/areas/reich/ pkatable/.
35. O. Andrey, A. Alexakis, G. Bernardinelli, Org. Lett. 2003, 5, 2559
36. S. Belot, S. Sulzer-Mosse, S. Kehrli, A. Alexakis, Chem. Commun. 2008, 4694. For one example of a cascade Michael/aldol reaction using α-imidazolylacetophenone proceeding through the iminium/enamine manifold see
37. W. Li, X. Li, W. Wu, X. Liang, J. Ye, Chem. Commun. 2011, 47, 8325. For one example of a Michael reaction of indolin-3-ones with enals under iminium catalysis see
38. Y.-Z. Liu, J. Zheng, P.-F. Xu, Y.-C. Luo, J. Org. Chem. 2011, 76, 7551.
39. M. Marigo, T. C. Wabnitz, D. Fielenbach,., K. A. Jørgensen, Angew. Chem. 2005, 117, 804
40. Angew. Chem. Int. Ed. 2005, 44, 794
41. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284
42. Angew. Chem. Int. Ed. 2005, 44, 4212.
43. For a related reaction reported in our group pertaining a similar oxa-Michael/intramolecular aldol reaction between α-hydroxy ketones and enals catalyzed by 3a see:, E. Reyes, G. Talavera, J. L. Vicario, D. Badia, L. Carrillo, Angew. Chem. 2009, 121, 5811
44. Angew. Chem. Int. Ed. 2009, 48, 5701. Relative and absolute stereostructures of compound 5 have been assigned asuming the same mechanistic pathway.
45. CCDC 910091 contains 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/data-request/cif.