An approach to the regioselective diamination of conjugated di- and trienes

Chemistry - A European Journal

Volumn 18, Issue 8, 2012, Pages 2212-2216

  Lishchynskyi, Anton ^a   Muñiz, Kilian ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

amination; amines; butadienes; diamination; iodine; oxidation

Indexed keywords

1 ,3 BUTADIENE; DIAMINATION; HYPERVALENT IODINE REAGENTS; OXIDATION PROCESS; REGIO-SELECTIVE;

AMINATION; AMINES; BUTADIENE; IODINE; OXIDATION;

REGIOSELECTIVITY;

EID: 84856878519     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103435     Document Type: Article

References (53)

1. F. Cardona, A. Goti, Nat. Chem. 2009, 1, 269
2. R. M. de Figueiredo, Angew. Chem. 2009, 121, 1212
3. Angew. Chem. Int. Ed. 2009, 48, 1190.
4. For the triamination of 1,5-butadienes to yield higher functionalized pyrrolidines, see:, V. Gõmez Aranda, J. Barluenga, F. Aznar, Synthesis 1974, 504.
5. K. B. Sharpless, S. P. Singer, J. Org. Chem. 1976, 41, 2504
6. M. Bruncko, T. A. V. Khuong, K. B. Sharpless, Angew. Chem. 1996, 108, 453
7. Angew. Chem. Int. Ed. Engl. 1996, 35, 454.
8. B. Akermark, J.-E. Bäckvall, A. Löwenborg, K. Zetterberg, J. Organomet. Chem. 1979, 166, C 33
9. for an intramolecular 1,4-cycloamination to form pyrroles, see:, J.-E. Bäckvall, J. E. Nyström, J. Chem. Soc. Chem. Commun. 1981, 59
10. J.-E. Bäckvall, Acc. Chem. Res. 1983, 16, 335.
11. H. Grennberg, J.-E. Bäckvall, in Transition Metals for Organic Synthesis Second Edition, Vol. 2, 2 nd ed., (Eds.: M. Beller, C. Bolm,), Wiley-VCH, Weinheim, 2004, pp. 243-265
12. J.-E. Bäckvall, in Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed., (Eds.: A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004, pp. 479-529.
13. G. L. J. Bar, G. C. Lloyd-Jones, K. I. Booker-Milburn, J. Am. Chem. Soc. 2005, 127, 7308.
14. For a related intramolecular diamination of butadienes, see:, K. Muñiz, J. Streuff, P. Chávez, C. H. Hövelmann, Chem. Asian J. 2008, 3, 1248.
15. H. Du, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007, 129, 762
16. H. Du, W. Yuan, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007, 129, 7496
17. H. Du, W. Yuan, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007, 129, 11688
18. B. Wang, H. Du, Y. Shi, Angew. Chem. 2008, 120, 8348
19. Angew. Chem. Int. Ed. 2008, 47, 8224
20. H. Du, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2008, 130, 8590
21. L. Xu, Y. Shi, J. Org. Chem. 2008, 73, 749
22. B. Zhao, H. Du, S. Cui, Y. Shi, J. Am. Chem. Soc. 2010, 132, 3523.
23. B. Zhao, H. Du, Y. Shi, J. Org. Chem. 2009, 74, 8392
24. W. Yuan, H. Du, B. Zhao, Y. Shi, Org. Lett. 2007, 9, 2589
25. B. Zhao, H. Du, Y. Shi, Org. Lett. 2008, 10, 1087
26. H. Du, B. Zhao, W. Yuan, Y. Shi, Org. Lett. 2008, 10, 4231
27. B. Zhao, X. Peng, S. Cui, Y. Shi, J. Am. Chem. Soc. 2010, 132, 11009
28. B. Zhao, X. Peng, S. Cui, Y. Shi, J. Am. Chem. Soc. 2010, 132, 11009
29. R. G. Cornwall, B. Zhao, Y. Shi, Org. Lett. 2011, 13, 434.
30. C. Röben, J. A. Souto, Y. González, A. Lishchynskyi, K. Muñiz, Angew. Chem. 2011, 123, 9650
31. Angew. Chem. Int. Ed. 2011, 50, 9478.
32. S. Schäfer, T. Wirth, Angew. Chem. 2010, 122, 2846
33. Angew. Chem. Int. Ed. 2010, 49, 2786, and references cited therein
34. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299
35. T. Dohi, Y. Kita, Chem. Commun. 2009, 2073
36. M. Uyanik, K. Ishihara, Chem. Commun. 2009, 2086
37. M. Ngatimin, D. W. Lupton, Aust. J. Chem. 2010, 63, 653
38. V. V. Zhdankin, ARKIVOC (Gainesville, FL, U.S.) 2009, 1, 1
39. Hypervalent Iodine in Organic Chemistry: Chemical Transformations (Eds.:, R. M. Moriarty, O. Prakash,), Wiley, New York, 2008
40. M. A. Ciufolini, N. A. Braun, S. Canesi, M. Ousmer, J. Chang, D. Chai, Synthesis 2007, 3759
41. M. Ochiai, Chem. Rec. 2007, 7, 12
42. Topics in Current Chemistry, Vol. 224 (Ed.:, T. Wirth,), Springer, Berlin, 2003.
43. R. D. Richardson, M. Desaize, T. Wirth, Chem. Eur. J. 2007, 13, 6745
44. J. Li, J.-L. Liang, P. W. H. Chan, C.-M. Che, Tetrahedron Lett. 2004, 45, 2685
45. J. Li, P. W. H. Chan, C.-M. Che, Org. Lett. 2005, 7, 5801
46. R. M. Moriarty, S. Tyagi, Org. Lett. 2010, 12, 364; bisazidation, see
47. R. Chung, E. Yu, C. D. Incarvito, D. J. Austin, Org. Lett. 2004, 6, 3881; aminooxygenation, see
48. B. M. Cochran, F. E. Michael, Org. Lett. 2008, 10, 5039
49. D. J. Wardrop, E. G. Bowen, R. E. Forslund, A. D. Sussman, S. L. Weerasekera, J. Am. Chem. Soc. 2010, 132, 1188
50. H. M. Lovick, F. E. Michael, J. Am. Chem. Soc. 2010, 132, 1249
51. A. Correa, I. Tellitu, E. Domínguez, R. SanMartin, J. Org. Chem. 2006, 71, 8316; for oxidative installation of a spiro carbon-nitrogen bond, see
52. T. Dohi, A. Maruyama, Y. Minamitsuji, N. Takenaga, Y. Kita, Chem. Commun. 2007, 1224.
53. J. D. Kim, O. P. Zee, Y. H. Jung, J. Org. Chem. 2003, 68, 3721.