Enantioselective H-bond-directing approach for trienamine-mediated reactions in asymmetric synthesis

Angewandte Chemie - International Edition

Volumn 51, Issue 36, 2012, Pages 9088-9092

  Albrecht, Łukasz ^a   Cruz Acosta, Fabio ^a   Fraile, Alberto ^a   Albrecht, Anna ^a   Christensen, Jannie ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

asymmetric synthesis; organocatalysis; synthetic methods; tetrahydroxanthones; trienamines

Indexed keywords

ASYMMETRIC SYNTHESIS; ORGANOCATALYSIS; SYNTHETIC METHODS; TETRAHYDROXANTHONES; TRIENAMINES;

REACTION KINETICS;

ENANTIOSELECTIVITY;

EID: 84865851339     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201204790     Document Type: Article

References (48)

1. H. Sailes, A. Whiting, J. Chem. Soc. Perkin Trans. 1 2000, 1785
2. K. Mikami, M. Shimizu, H.-C. Zhang, B. E. Maryanoff, Tetrahedron 2001, 57, 2917
3. J. Clayden, N. Vassiliou, Org. Biomol. Chem. 2006, 4, 2667
4. E. J. Thomas, Chem. Rec. 2007, 7, 115
5. J. Clayden, Chem. Soc. Rev. 2009, 38, 817.
6. K. Tatsuta, S. Hosokawa, Chem. Rev. 2005, 105, 4707
7. S. Sezer, D. Özdemirhan, E. Şahin, C. Tanyeli, Tetrahedron: Asymmetry 2006, 17, 2981
8. K. Liu, A. Chougnet, W.-D. Woggon, Angew. Chem. 2008, 120, 5911
9. Angew. Chem. Int. Ed. 2008, 47, 5827
10. C. A. Lewis, J. L. Gustafson, A. Chiu, J. Balsells, D. Pollard, J. Murry, R. A. Reamer, K. B. Hansen, S. J. Miller, J. Am. Chem. Soc. 2008, 130, 16358.
11. D. B. Ramachary, Y. V. Reddy, Eur. J. Org. Chem. 2012, 865; for selected examples, see
12. S. Bertelsen, M. Marigo, S. Brandes, P. Dinér, K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 12973
13. G. Bergonzini, S. Vera, P. Melchiorre, Angew. Chem. 2010, 122, 9879
14. Angew. Chem. Int. Ed. 2010, 49, 9685
15. J. Stiller, E. Marqués-Lõpez, R. P. Herrera, R. Fröhlich, C. Strohmann, M. Christmann, Org. Lett. 2011, 13, 70
16. J.-L. Li, S.-L. Zhou, P.-X. Chen, L. Dong, T.-Y. Liu, Y.-C. Chen, Chem. Sci. 2012, 3, 1879
17. Ś. Albrecht, G. Dickmeiss, F. Cruz Acosta, C. Rodríguez- Escrich, R. L. Davis, K. A. Jørgensen, J. Am. Chem. Soc. 2012, 134, 2543
18. G. Talavera, E. Reyes, J. L. Vicario, L. Carrillo, Angew. Chem. 2012, 124, 4180
19. Angew. Chem. Int. Ed. 2012, 51, 4104.
20. E. Arceo, P. Melchiorre, Angew. Chem. 2012, 124, 5384
21. Angew. Chem. Int. Ed. 2012, 51, 5290; for examples, see
22. Z.-J. Jia, H. Jiang, J.-L. Li, B. Gschwend, Q.-Z. Li, X. Yin, J. Grouleff, Y.-C. Chen, K. A. Jørgensen, J. Am. Chem. Soc. 2011, 133, 5053
23. H. Jiang, B. Gschwend, Ś. Albrecht, S. G. Hansen, K. A. Jørgensen, Chem. Eur. J. 2011, 17, 9032
24. Z.-J. Jia, Q. Zhou, Q.-Q. Zhou, P.-Q. Chen, Y.-C. Chen, Angew. Chem. 2011, 123, 8797
25. Angew. Chem. Int. Ed. 2011, 50, 8638
26. Y.-K. Liu, M. Nappi, E. Arceo, S. Vera, P. Melchiorre, J. Am. Chem. Soc. 2011, 133, 15212
27. Y. Liu, M. Nappi, E. C. Escudero-Adán, P. Melchiorre, Org. Lett. 2012, 14, 1310.
28. G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79
29. A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922
30. L.-W. Xu, L. Li, Z.-H. Shi, Adv. Synth. Catal. 2010, 352, 243
31. L. Z. Zimmer, C. Sparr, R. Gilmaur, Angew. Chem. 2011, 123, 12062
32. Angew. Chem. Int. Ed. 2011, 50, 11860
33. K. L. Jensen, G. Dickmeiss, H. Jiang, Ś. Albrecht, K. A. Jørgensen, Acc. Chem. Res. 2012, 45, 248.
34. K.-S. Masters, S. Bräse, Chem. Rev. 2012, 112, 3717
35. R. N. Kharwar, A. Mishra, S. K. Gond, A. Stierle, D. Stierle, Nat. Prod. Rep. 2011, 28, 1208.
36. R. Andersen, G. Buechi, B. Kobbe, A. L. Demain, J. Org. Chem. 1977, 42, 352
37. K. C. Nicolaou, A. Li, Angew. Chem. 2008, 120, 6681
38. Angew. Chem. Int. Ed. 2008, 47, 6579
39. M. E. Maier, Nat. Prod. Rep. 2009, 26, 1105.
40. R. P. Hsung, J. Org. Chem. 1997, 62, 7904
41. S. J. Degen, H. C. Shen, G. M. Golding, C. A. Zificsak, R. P. Hsung, Bioorg. Med. Chem. Lett. 1999, 9, 973.
42. R. I. Storer, C. Aciro, L. H. Jones, Chem. Soc. Rev. 2011, 40, 2330
43. J. Alemán, A. Parra, H. Jiang, K. A. Jørgensen, Chem. Eur. J. 2011, 17, 6890; for the seminal report on squaramide-based catalysts in enantioselective synthesis, see
44. J. P. Malerich, K. Hagihara, V. H. Rawal, J. Am. Chem. Soc. 2008, 130, 14416.
45. See the Supporting Information for the crystal structures. CCDC 886343 and 886348 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/data-request/cif.
46. S. J. Zuend, M. P. Coughlin, M. P. Lalonde, E. N. Jacobsen, Nature 2009, 461, 968; for a review on H-bond strengths, see
47. T. Steiner, Angew. Chem. 2002, 114, 50
48. Angew. Chem. Int. Ed. 2002, 41, 48.