Highly enantioselective [3+2] cycloaddition of vinylcyclopropane with nitroalkenes catalyzed by palladium(0) with a chiral bis(tert-amine) ligand

Chemistry - A European Journal

Volumn 21, Issue 6, 2015, Pages 2335-2338

  Wei, Feng ^a,b   Ren, Chuan Li ^a,b   Wang, Dong ^a   Liu, Li ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Asymmetric catalysis; Cycloaddition; Nitroalkenes; Palladium catalyst; Vinylcyclopropane

Indexed keywords

CATALYSIS; CATALYSTS; CYCLOADDITION; ENANTIOSELECTIVITY; LIGANDS;

ASYMMETRIC CATALYSIS; DIASTEREOSELECTIVITIES; EFFICIENT CATALYSTS; NITROALKENES; PALLADIUM CATALYST; PALLADIUM COMPLEXES; VINYLCYCLOPROPANE; [3+2]-CYCLOADDITION;

PALLADIUM COMPOUNDS;

EID: 84921507667     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201405407     Document Type: Article

References (46)

1. a) K. V. Gothelf, K. A. Joørgensen, Chem. Rev. 1998, 98, 863-910
2. b) A. Padwa, W. H. Pearson, Synthetic applications of 1, 3-dipolar cycloaddition chemistry toward heterocycles and natural products, Vol. 59, Wiley, 2003
3. c) G. Pandey, P. Banerjee, S. R. Gadre, Chem. Rev. 2006, 106, 4484-4517
4. d) N. A. Bokach, M. L. Kuznetsov, V. Y. Kukushkin, Coord. Chem. Rev. 2011, 255, 2946-2967
5. e) S. Yu, S. Ma, Angew. Chem. Int. Ed. 2012, 51, 3074-3112
6. Angew. Chem. 2012, 124, 3128-3167.
7. a) H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151-1196
8. b) M. Yu, B. L. Pagenkopf, Tetrahedron 2005, 61, 321-347
9. c) M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117-3179
10. d) C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, 3051-3060
11. e) S. Liao, X.-L. Sun, Y. Tang, Acc. Chem. Res. 2014, 47, 2260-2272
12. f) T. F. Schneider, J. Kaschel, D. B. Werz, Angew. Chem. Int. Ed. 2014, 53, 5504-5523
13. Angew. Chem. 2014, 126, 5608-5628.
14. a) I. Shimizu, Y. Ohashi, J. Tsuji, Tetrahedron Lett. 1985, 26, 3825-3828
15. b) A. T. Parsons, M. J. Campbell, J. S. Johnson, Org. Lett. 2008, 10, 2541-2544.
16. a) R. K. Bowman, J. S. Johnson, Org. Lett. 2006, 8, 573-576
17. b) R. Tombe, T. Kurahashi, S. Matsubara, Org. Lett. 2013, 15, 1791-1793.
18. A. P. Dieskau, M. S. Holzwarth, B. Plietker, J. Am. Chem. Soc. 2012, 134, 5048-5051.
19. J. Moran, A. G. Smith, R. M. Carris, J. S. Johnson, M. J. Krische, J. Am. Chem. Soc. 2011, 133, 18618-18621.
20. L. Jiao, Z.-X. Yu, J. Org. Chem. 2013, 78, 6842-6848.
21. a) A. F. G. Goldberg, B. M. Stoltz, Org. Lett. 2011, 13, 4474-4476
22. b) B. M. Trost, P. J. Morris, Angew. Chem. Int. Ed. 2011, 50, 6167-6170
23. Angew. Chem. 2011, 123, 6291-6294
24. c) L.-y. Mei, Y. Wei, Q. Xu, M. Shi, Organometallics 2012, 31, 7591-7599
25. d) B. M. Trost, P. J. Morris, S. J. Sprague, J. Am. Chem. Soc. 2012, 134, 17823-17831.
26. a) K. Yamamoto, T. Ishida, J. Tsuji, Chem. Lett. 1987, 16, 1157-1158
27. b) L.-y. Mei, Y. Wei, Q. Xu, M. Shi, Organometallics 2013, 32, 3544-3556.
28. N. Ono in The Nitro Group in Organic Synthesis, Wiley, 2002, pp. 231-301.
29. a) N. Takenaka, R. S. Sarangthem, S. K. Seerla, Org. Lett. 2007, 9, 2819-2822
30. b) X.-Y. Guan, Y. Wei, M. Shi, Org. Lett. 2010, 12, 5024-5027
31. c) M. Rueping, A. Kuenkel, R. Fröhlich, Chem. Eur. J. 2010, 16, 4173-4176
32. d) B. M. Trost, D. A. Bringley, P. S. Seng, Org. Lett. 2012, 14, 234-237
33. e) K. Albertshofer, B. Tan, C. F. Barbas, Org. Lett. 2012, 14, 1834-1837
34. f) B.-C. Hong, P.-Y. Chen, P. Kotame, P.-Y. Lu, G.-H. Lee, J.-H. Liao, Chem. Commun. 2012, 48, 7790-7792
35. g) B. M. Trost, D. A. Bringley, B. M. O'Keefe, Org. Lett. 2013, 15, 5630-5633.
36. a) G. Feuer in Progress in Medicinal Chemistry, Vol. 10 (Eds.: G. P. Ellis, G. B. West), Elsevier, 1974, pp. 85-58
37. b) K. A. Bello, L. Cheng, J. Griffiths, J. Chem. Soc. Perkin Trans. 2 1987, 815-818
38. c) D. Leblois, S. Piessard, G. Le Baut, P. Kumar, J.-D. Brion, L. Sparfel, R.-Y. Sanchez, M. Juge, J.-Y. Petit, L. Welin, Eur. J. Med. Chem. 1987, 22, 229-238
39. d) M. R. Bryce, S. R. Davies, M. Hasan, G. J. Ashwell, M. Szablewski, M. G. B. Drew, R. Short, M. B. Hursthouse, J. Chem. Soc. Perkin Trans. 2 1989, 1285-1292
40. e) D. B. Hansen, M. M. Joullie, Chem. Soc. Rev. 2005, 34, 408-417.
41. a) D. L. Boger, I. C. Jacobson, J. Org. Chem. 1990, 55, 1919-1928
42. b) J. A. Wendt, P. J. Gauvreau, R. D. Bach, J. Am. Chem. Soc. 1994, 116, 9921-9926.
43. B. A. Brooks, E. M. Blair, R. Finch, A. F. Lant, Br. J. Clin. Pharmacol. 1980, 10, 249-258.
44. a) J.-L. Vasse, R. Stranne, R. Zalubovskis, C. Gayet, C. Moberg, J. Org. Chem. 2003, 68, 3258-3270
45. b) R. Zalubovskis, A. Bouet, E. Fjellander, S. Constant, D. Linder, A. Fischer, J. Lacour, T. Privalov, C. Moberg, J. Am. Chem. Soc. 2008, 130, 1845-1855.
46. The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.