Enantioselective intermolecular crossed-conjugate additions between nitroalkenes andα,β-enals through a dual activation strategy

Angewandte Chemie - International Edition

Volumn 48, Issue 7, 2009, Pages 1279-1282

  Zhong, Cheng ^a   Chen, Yunfeng ^a   Petersen, Jeffrey L ^a   Akhmedov, Novruz G ^a   Shi, Xiaodong ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

asymmetric catalysis; enantioselectivity; Lewis bases; pyrrolidines

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY;

ASYMMETRIC CATALYSIS; CONJUGATE ADDITIONS; DUAL ACTIVATIONS; ENANTIOSELECTIVE; LEWIS BASES; NITROALKENES; PYRROLIDINE; PYRROLIDINES;

ELECTRON TRANSITIONS;

EID: 60149088814     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805558     Document Type: Article

References (34)

1. For recent reviews, see: a) J. L. Vicario, D. Badia, L. Carrillo, Synthesis 2007, 2065-2092;
2. b) O. Andrey, A. Alexakis, A. Tomassini, G. Bernardinelli, Adv. Synth. Catal. 2004, 346, 1147-1168;
3. c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894.
4. For recent reviews, see: a) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716-4739;
5. Angew. Chem. Int. Ed. 2008, 47, 4638-4660;
6. b) K. N. Houk, B. List, Acc. Chem. Res. 2004, 37, 487-487;
7. c) Y. Hayashi, J. Syn. Org. Chem. Jpn. 2005, 63, 464-477.
8. For review of iminium catalysis, see: a) G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006, 39, 79-87;
9. b) S. Brandau, A. Landa, J. Franzen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2006, 118, 4411-4415;
10. Angew. Chem. Int. Ed. 2006, 45, 4305-4309;
11. c) W. Notz, F. Tanaka, C. F. Barbas, Acc. Chem. Res. 2004, 37, 580-591.
12. Recent review, see: a) D. Enders, C. Grondal, M. R. M. Huttl, Angew. Chem. 2007, 119, 1590-1601;
13. Angew. Chem. Int. Ed. 2007, 46, 1570-1581.
14. Selected examples, see: b) A. Carlone, S. Cabrera, M. Marigo, K. A. J0rgensen, Angew. Chem. 2007, 119, 1119-1122;
15. Angew. Chem. Int. Ed. 2007, 46, 1101-1104;
16. c) D. Enders, M. R. M. Huttl, C. Grondal, G. Raabe, Nature 2006, 441, 861-863;
17. d) J. Wang, H. X. Xie, H. Li, L. S. Zu, W. Wang, Angew. Chem. 2008, 120, 4245-4247;
18. Angew. Chem. Int. Ed. 2008, 47, 4177-4179.
19. D. Basavaiah, K. V. Rao, R. J. Reddy, Chem. Soc. Rev. 2007, 36, 1581-1588.
20. Some recent examples, see: a) S. E. Denmark, G. L. Beutner, Angew. Chem. 2008, 120, 1584-1663;
21. Angew. Chem. Int. Ed. 2008, 47, 1560-1638;
22. b) B. J. Cowen, S. J. Miller, J. Am. Chem. Soc. 2007, 129, 10988-10989;
23. c) S. L. Wiskur, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 6176-6177;
24. d) G. S. Creech, O. Kwon, Org. Lett. 2008, 10, 429-432;
25. e) H. F. Duan, X. H. Sun, W. Y. Liao, J. L. Petersen, X. D. Shi, Org. Lett. 2008, 10, 4113-4116.
26. X. H. Sun, S. Sengupta, J. L. Petersen, H. Wang, J. P. Lewis, X. D. Shi, Org. Lett. 2007, 9, 4495-4498.
27. Intramolecular examples, see: a) V. Sriramurthy, G. A. Barcan, O. Kwon, J. Am. Chem. Soc. 2007, 129, 12928-12929;
28. b) L. C. Wang, A. L. Luis, K. Agaplou, H. Y. Jang, M. J. Krische, J. Am. Chem. Soc. 2002, 124, 2402-2403.
29. Intermolecular example, see: c) M. Dadwal, R. Mohan, D. Panda, S. M. Mobin, I. N. N. Namboothiri, Chem. Commun. 2006, 338-340.
30. The stereochemistry of the products was assigned based on the X-ray crystal structures of 4e and 6a. CCDC 704977 (cis-4e), 704978 (trans-4e), 704979 (6a), and 704980 (trans-6a) 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.
31. For recent examples, see: a) E. Reyes, H. Jiang, A. Milelli, P. Elsner, R. G. Hazell, K. A. Jørgensen, Angew. Chem. 2007, 119, 9362-9365;
32. Angew. Chem. Int. Ed. 2007, 46, 9202-9205;
33. b) Y. Hayashi, T. Itoh, M. Ohkubo, H. Ishikawa, Angew. Chem. 2008, 120, 4800-4802;
34. Angew. Chem. Int. Ed. 2008, 47, 4722-4724.