One-pot enantioselective aziridination of olefins catalyzed by a copper(I) complex of a novel diimine ligand by using PhI(OAc)2 and sulfonamide as nitrene precursors

Chemistry - A European Journal

Volumn 12, Issue 17, 2006, Pages 4568-4575

  Wang, Xisheng ^a   Ding, Kuiling ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric catalysis; Aziridination; Copper; D mannitol; Diimine; One pot reaction

Indexed keywords

AZIRIDINATION; D-MANNITOL; DIIMINE; ONE-POT REACTION; RADICAL IONS;

COPPER; NITROGEN COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

OLEFINS;

ALKENE; AZIRIDINE; AZIRIDINE DERIVATIVE; COPPER; IMINE; LIGAND; PHENYLNITRENE; SULFONAMIDE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALKENES; AZIRIDINES; CATALYSIS; COPPER; IMINES; LIGANDS; STEREOISOMERISM; SULFONAMIDES;

EID: 33745121905     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501109     Document Type: Article

References (54)

1. For comprehensive reviews on asymmetric azirindination see: a) E. N. Jacobsen in Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Vol. II, Springer, Berlin, 1999, Chapter 17;
2. b) T. Katsuki in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, pp. 283-325;
3. c) A. H. Li, L. X. Dai, A. K. Aggarwal, Chem. Rev. 1997, 97, 2341-2372;
4. d) P. Muller, C. Fruit, Chem. Rev. 2003, 103, 2905-2919;
5. e) H. M. I. Osborn, J. Sweeney, Tetrahedron: Asymmetry 1997, 8, 1693-1715.
6. a) D. Tanner, Pure Appl. Chem. 1993, 65, 1319-1328;
7. b) D. Tanner, Angew. Chem. 1994, 106, 625-643;
8. Angew. Chem. Int. Ed. Engl. 1994, 33, 599-619;
9. c) W. McCoull, Synthesis 2000, 1347-1365;
10. d) T. Hudlicky, X. Tian, K. Königsberger, R. Maurya, J. Rouden, B. Fan, J. Am. Chem. Soc. 1996, 118, 10752-10765;
11. e) C. E. Masse, B. S. Knight, P. Stavropoulos, J. S. Panek, J. Am. Chem. Soc. 1997, 119, 6040-6047;
12. f) L. E. Overman, A. L. Tomasi, J. Am. Chem. Soc. 1998, 120, 4039-4040;
13. g) A. Sudau, W. Müunch, J. W. Bats, U. Nubbemeyer, Chem. Eur. J. 2001, 7, 611-621.
14. a) D. Mansuy, J.-P. Mahy, A. Dureault, G. Bedi, P. Battioni, J. Chem. Soc., Chem. Commun. 1984, 1161-1163;
15. b) T.-S. Lai, H.-L. Kwong, C.-M. Che, S.-M. Peng, Chem. Commun. 1997, 2373-2735;
16. c) K. Noda, N. Hosoya, R. Irie, Y. Ito, T. Katuski, Synlett 1993, 469-471;
17. d) H. Nishikori, T. Katsuki, Tetrahedron Lett. 1996, 37, 9245-9248;
18. e) S. Minakata, T. Ando, M. Nishimura, I. Ryu, M. Komatsu, Angew. Chem. 1998, 110, 3596-3598;
19. Angew. Chem. Int. Ed. 1998, 37, 3392-3394.
20. a) D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728;
21. b) D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson, D. M. Barnes, J. Am. Chem. Soc. 1993, 115, 5328-5329;
22. c) Z. Li, K. R. Conser, E. N. Jacobsen, J. Am. Chem. Soc. 1993, 115, 5326-5327;
23. d) Z. Li, R. W. Quan, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5889-5890;
24. e) R. W. Quan, Z. Li, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 8156-8157;
25. f) M. Shi, N. Itoh, Y. Masaki, J. Chem. Res. S. 1996, 352-356.
26. For recent examples see: a) C. J. Sanders, K. M. Gillespie, D. Bell, P. Scott, J. Am. Chem. Soc. 2000, 122, 7132-7133;
27. b) M. Shi, C.J. Wang, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 3105-3111;
28. c) K. M. Gillespie, E. J. Crust, R. J. Deeth, P. Scott, Chem. Commun. 2001, 785-786;
29. d) M. Shi, C.J. Wang, Chirality 2002, 14, 412-416;
30. e) K. M. Gillespie, C. J. Sanders, P. O'Shaughnessy, I. Westmoreland, C. P. Thickitt, P. Scott, J. Org. Chem. 2002, 67, 3450-3458;
31. f) F. Duran, L. Leman, A. Ghini, G. Burton, P. Dauban, R. H. Dodd, Org. Lett. 2002, 4, 2481-2483;
32. g) J. Xu, L. Ma, P. Jiao, Chem. Commun. 2004, 1616-1617;
33. h) F. Mohr, S. A. Binfield, J. C. Fettinger, A. N. Vedernikov, J. Org. Chem. 2005, 70, 4833-4839;
34. i) H. Suga, A. Kakehi, S. Ito, T. Ibata, T. Fudo, Y. Watanabe, Y. Kinoshita, Bull. Chem. Soc. Jpn. 2003, 76, 189-199.
35. a) P. Dauban, L. Saniére, A. Tarrade, R. H. Dodd, J. Am. Chem. Soc. 2001, 123, 7707-7708;
36. b) H.-L. Kwong, D. Liu, K.-Y. Chan, C.-S. Lee, K.-H. Huang, C.-M. Che, Tetrahedron Lett. 2004, 45, 3965-3968.
37. a) M. J. Sodergren, D. A. Alonso, P. G. Andersson, Tetrahedron: Asymmetry 1997, 5, 3563-3565;
38. b) P.J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178.
39. Y. L. Merrer, A. Dureault, C. Greck, D. Micas-Languin, C. Gravier, J. Depazay, Heterocycles 1987, 25, 541-548.
40. R. Zhang, L. Yu, L. Xu, Z. Wang, K. Ding, Tetrahedron Lett. 2001, 42, 7659-7662.
41. CCDC-283046 (3a) and -283047 (11f) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/ data_request/cif.
42. D. A. Evans, M. M. Margaret, M. T. Bilodeau, J. Org. Chem. 1991, 56, 6744-6746.
43. For examples of chiral diamines in asymmetric catalysis see: a) D. Lucet, T. L. Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772;
44. Angew. Chem. Int. Ed. 1998, 37, 2580-2627;
45. b) M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938;
46. c) F.-Y. Zhang, C.-C. Pai, A. S. C. Chan, J. Am. Chem. Soc. 1998, 120, 5808-5809;
47. d) M. T. Reetz, E. Bohres, R. Coddard, Chem. Commun. 1998, 8, 935-937;
48. e) S. E. Denmark, T. Wynn, J. Am. Chem. Soc. 2001, 123, 6199-6200;
49. f) M. T. Reetz, G. Haderiein, K. Angermund, J. Am. Chem. Soc. 2000, 122, 996-997;
50. g) D. A. Evans, J. M. Janey, N. Magomedov, J. S. Tedrow, Angew. Chem. 2001, 113, 1936-1940;
51. Angew. Chem. Int. Ed. 2001, 40, 1884-1888;
52. h) A. Berkessel, D. Menche, C. A. Sklorz, M. Schröder, I. Paterson, Angew. Chem. 2003, 115, 1062-1065;
53. Angew. Chem. Int. Ed. 2003, 42, 1032-1035:
54. i) M. Shi, C. J. Wang, W. Zhang, Chem. Eur. J. 2004, 10, 5507-5516.