Trienamine catalysis with 2,4-dienones: Development and application in asymmetric Diels-Alder reactions

Angewandte Chemie - International Edition

Volumn 51, Issue 18, 2012, Pages 4401-4404

  Xiong, Xiao Feng ^a   Zhou, Quan ^a   Gu, Jing ^a   Dong, Lin ^a   Liu, Tian Yu ^b   Chen, Ying Chun ^a,b  

^a SICHUAN UNIVERSITY   (China)

^b THIRD MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

2,4 dienones; asymmetric synthesis; Diels Alder reaction; homogeneous catalysis; trienamines

Indexed keywords

2,4-DIENONES; ASYMMETRIC SYNTHESIS; DIELS-ALDER REACTION; HOMOGENEOUS CATALYSIS; TRIENAMINES;

CYCLOADDITION; OLEFINS; REACTION KINETICS;

CATALYSIS;

ACETONITRILE DERIVATIVE; BIPHENYL DERIVATIVE; CYCLOHEXENE DERIVATIVE; DIENONE A; ENAMINE; IMIDAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM;

ACETONITRILES; BIPHENYL COMPOUNDS; CATALYSIS; CYCLIZATION; CYCLOHEXENES; IMIDAZOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84860119030     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201200248     Document Type: Article

References (46)

1. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395
2. W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386
3. B. List, J. Am. Chem. Soc. 2000, 122, 9336
4. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243
5. W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874
6. K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260.
7. A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416
8. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471
9. P. Melchiorre, Angew. Chem. 2009, 121, 1386
10. Angew. Chem. Int. Ed. 2009, 48, 1360
11. S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178
12. C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167
13. P. M. Pihko, I. Majander, A. Erkkilä, Top. Curr. Chem. 2010, 292, 29.
14. 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
15. Z.-J. Jia, Q. Zhou, Q.-Q. Zhou, P.-Q. Chen, Y.-C. Chen, Angew. Chem. 2011, 123, 8797
16. Angew. Chem. Int. Ed. 2011, 50, 8638
17. H. Jiang, B. Gschwend, Å. Albrecht, S. G. Hansen, K. A. Jørgensen, Chem. Eur. J. 2011, 17, 9032
18. Y. Liu, M. Nappi, E. Arceo, S. Vera, P. Melchiorre, J. Am. Chem. Soc. 2011, 133, 15212.
19. Y.-C. Chen, Synlett 2008, 1919
20. L. Jiang, Y.-C. Chen, Catal. Sci. Technol. 2011, 1, 354
21. G. Bartoli, P. Melchiorre, Synlett 2008, 1759; for selected examples, see
22. J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393
23. Angew. Chem. Int. Ed. 2007, 46, 389
24. W. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen, Angew. Chem. 2007, 119, 7811
25. Angew. Chem. Int. Ed. 2007, 46, 7667
26. R. P. Singh, K. Bartelson, Y. Wang, H. Su, X. Lu, L. Deng, J. Am. Chem. Soc. 2008, 130, 2422
27. J. Zhou, V. Wakchaure, P. Kraft, B. List, Angew. Chem. 2008, 120, 7768
28. Angew. Chem. Int. Ed. 2008, 47, 7656
29. E. Zhang, C.-A. Fan, Y.-Q. Tu, F.-M. Zhang, Y.-L. Song, J. Am. Chem. Soc. 2009, 131, 14626
30. L.-Y. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7332
31. Angew. Chem. Int. Ed. 2009, 48, 7196
32. G. Bergonzini, S. Vera, P. Melchiorre, Angew. Chem. 2010, 122, 9879
33. Angew. Chem. Int. Ed. 2010, 49, 9685
34. G. Bergonzini, S. Vera, P. Melchiorre, Angew. Chem. 2010, 122, 9879
35. Angew. Chem. Int. Ed. 2010, 49, 9685
36. Q. Cai, C. Zheng, J.-W. Zhang, S.-L. You, Angew. Chem. 2011, 123, 8824
37. Angew. Chem. Int. Ed. 2011, 50, 8665.
38. For a discussion on orbital-energy control of cycloaddition reactivity, see:, R. Sustmann, Pure Appl. Chem. 1974, 40, 569.
39. In contrast, an α-methyl-2,4-dienone with a δ,δ- disubstituted pattern still exhibited no reactivity under the same conditions, see the Supporting Information.
40. G. Bencivenni, P. Galzerano, A. Mazzanti, G. Bartoli, P. Melchiorre, Proc. Natl. Acad. Sci. USA 2010, 107, 20642.
41. More 2,4-dienones without δ,δ-disubstituted patterns have been tested, but only the noncatalyzed DA cycloadducts were obtained, see the Supporting Information.
42. CCDC 864374 (6h) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
43. R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97
44. (R,R)-TsDPEN-Ru complex is a mismatched catalyst for chiral compound 6d, and poor conversion was obtained
45. The absolute configuration of the newly generated alcohol in product 13 was assigned on the basis of the well-established reaction model of Noyori's asymmetric transfer-hydrogenation system.
46. E. M. Stang, M. C. White, J. Am. Chem. Soc. 2011, 133, 14892.