Enantiospecific allylic alkylation of substituted hydrazines with allylic alcohols

Chinese Journal of Organic Chemistry

Volumn 35, Issue 3, 2015, Pages 618-624

  Xu, Jing Kun ^a   Gu, Yonghong ^a   Tian, Shi Kai ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Alcohols; Allylic alkylation; Enantiospecificity; Hydrazines; Palladium

Indexed keywords

EID: 84928390754     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: 10.6023/cjoc201412049     Document Type: Article

References (68)

1. Tsuji, J. Acc. Chem. Res. 1969, 2, 144.
2. Trost, B. M. Tetrahedron 1977, 33, 2615.
3. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
4. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
5. Kazmaier, U.; Pohlman, M. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Eds.: de Meijere, A.; Diederich, F., Wiley-VCH, Weinheim, 2004, p. 531.
6. Muzart, J. Tetrahedron 2005, 61, 4179.
7. Bandini, M. Angew. Chem., Int. Ed. 2011, 50, 994.
8. Sundararaju, B.; Achard, M.; Bruneau, C. Chem. Soc. Rev. 2012, 41, 4467.
9. Bandini, M.; Cera, G.; Chiarucci, M. Synthesis 2012, 44, 504.
10. Ye, J.; Zhao, J.; Xu, J.; Mao, Y.; Zhang, Y. J. Chem. Commun. 2013, 49, 9761.
11. Wu, H.-B.; Ma, X.-T.; Tian, S.-K. Chem. Commun. 2014, 50, 219.
12. Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 10968.
13. Roggen, M.; Carreira, E. M. J. Am. Chem. Soc. 2010, 132, 11917.
14. Mukherjee, P.; Widenhoefer, R. A. Org. Lett. 2010, 12, 1184.
15. Kawai, N.; Abe, R.; Uenishi, J. Tetrahedron Lett. 2009, 50, 6580.
16. Hande, S. M.; Kawai, N.; Uenishi, J. J. Org. Chem. 2009, 74, 244.
17. Kawai, N.; Abe, R.; Matsuda, M.; Uenishi, J. J. Org. Chem. 2011, 76, 2102.
18. Mukherjee, P.; Widenhoefer, R. A. Org. Lett. 2011, 13, 1334.
19. Mukherjee, P.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2012, 51, 1405.
20. Vikhe, Y. S.; Hande, S. M.; Kawai, N.; Uenishi, J. J. Org. Chem. 2009, 74, 5174.
21. Mukherjee, P.; Widenhoefer, R. A. Chem.-Eur. J. 2013, 19, 3437.
22. Uenishi, J.; Ohmi, M.; Ueda, A. Tetrahedronn: Asymmetry 2005, 16, 1299.
23. Kawai, N.; Lagrange, J.-M.; Ohmi, M.; Uenishi, J. J. Org. Chem. 2006, 71, 4530.
24. Kawai, N.; Lagrange, J.-M.; Uenishi, J. Eur. J. Org. Chem. 2007, 2808.
25. Uenishi, J.; Vikhe, Y. S.; Kawai, N. Chem. Asian J. 2008, 3, 473.
26. Guérinot, A.; Serra-Muns, A.; Bensoussan, C.; Reymond, S.; Cossy, J. Tetrahedron 2011, 67, 5024.
27. Unsworth, W. P.; Stevens, K.; Lamont, S. G.; Robertson, J. Chem. Commun. 2011, 47, 7659.
28. Ghebreghiorgis, T.; Biannic, B.; Kirk, B. H.; Ess, D. H.; Aponick, A. J. Am. Chem. Soc. 2012, 134, 16307.
29. Ghebreghiorgis, T.; Kirk, B. H.; Aponick, A.; Ess, D. H. J. Org. Chem. 2013, 78, 7664.
30. Ma, X.-T.; Dai, R.-H.; Zhang, J.; Gu, Y.; Tian, S.-K. Adv. Synth. Catal. 2014, 356, 2984.
31. Lumbroso, A.; Cooke, M. L.; Breit, B. Angew. Chem., Int. Ed. 2013, 52, 1890.
32. Tšupova, S.; Mäeorg, U. Org. Lett. 2013, 15, 3381.
33. Zhang, R.; Durkin, J. P.; Windsor, W. T. Bioorg. Med. Chem. Lett. 2002, 12, 1005.
34. Raja, A.; Lebbos, J.; Kirkpatrick, P. Nat. Rev. Drug Discovery 2003, 1, 857.
35. Ragnarsson, U. Chem. Soc. Rev. 2001, 30, 205.
36. Friestad, G. K. Eur. J. Org. Chem. 2005, 3157.
37. Strick, B. F.; Mundal, D. A.; Thomson, R. J. J. Am. Chem. Soc. 2011, 133, 14252.
38. Lutz, K. E.; Thomson, R. J. Angew. Chem., Int. Ed. 2011, 50, 4437.
39. Gutierrez, O.; Strick, B. F.; Thomson, R. J.; Tantillo, D. J. Chem. Sci. 2013, 4, 3997.
40. Reddel, J. C. T.; Lutz, K. E.; Diagne, A. B.; Thomson, R. J. Angew. Chem., Int. Ed. 2014, 53, 1395.
41. Yamagishi, T.; Ohnuki, M.; Kiyooka, T.; Masui, D.; Sato, K.; Yamaguchi, M. Tetrahedron: Asymmetry 2003, 14, 3275.
42. Kloetzing, R. J.; Knochel, P. Tetrahedron: Asymmetry 2006, 17, 116.
43. Popa, D.; Marcos, R.; Sayalero, S.; Vidal-Ferran, A.; Pericàs, M. A. Adv. Synth. Catal. 2009, 351, 1539.
44. Yuan, H.; Zhou, Z.; Xiao, J.; Liang, L.; Dai, L. Tetrahedron: Asymmetry 2010, 21, 1874.
45. Li, H.-H.; Dong, D.-J.; Tian, S.-K. Eur. J. Org. Chem. 2008, 3623.
46. Li, H.-H.; Jin, Y.-H.; Wang, J.-Q.; Tian, S.-K. Org. Biomol. Chem. 2009, 7, 3219.
47. Yang, C.-F.; Shen, C.; Li, H.-H.; Tian, S.-K. Chin. Sci. Bull. 2012, 57, 2377.
48. Tian, Y.; Sui, Y.; Gu, Y.; Tian, S.-K. Adv. Synth. Catal. 2012, 354, 3475.
49. Li, M.-B.; Wang, Y.; Tian, S.-K. Angew. Chem., Int. Ed. 2012, 51, 2968.
50. Wu, X.-S.; Chen, Y.; Li, M.-B.; Zhou, M.-G.; Tian, S.-K. J. Am. Chem. Soc. 2012, 134, 14694.
51. Li, M.-B.; Li, H.; Wang, J.; Liu, C.-R.; Tian, S.-K. Chem. Commun. 2013, 49, 8190.
52. Ma, X.-T.; Wang, Y.; Dai, R.-H.; Liu, C.-R.; Tian, S.-K. J. Org. Chem. 2013, 78, 11071.
53. Wu, X.-S.; Zhou, M.-G.; Chen, Y.; Tian, S.-K. Asian J. Org. Chem. 2014, 3, 711.
54. Wang, T.-T.; Wang, F.-X.; Yang, F.-L.; Tian, S.-K. Chem. Commun. 2014, 50, 3802.
55. Zhou, M.-G.; Zhang, W.-Z.; Tian, S.-K. Chem. Commun. 2014, 50, 14531.
56. Wang, Y.; Li, M.; Ma, X.; Liu, C.; Gu, Y.; Tian, S.-K. Chin. J. Chem. 2014, 32, 741.
57. Wang, Y.; Xu, J.-K.; Gu, Y.; Tian, S.-K. Org. Chem. Front. 2014, 1, 812.
58. Bertelsen, S.; Marigo, M.; Brandes, S.; Dinér, P.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 12973.
59. Wang, J.; Chen, J.; Kee, C. W.; Tan, C.-H. Angew. Chem., Int. Ed. 2012, 51, 2382.
60. Yang, F.-L.; Ma, X.-T.; Tian, S.-K. Chem.-Eur. J. 2012, 18, 1582.
61. Yang, F.-L.; Tian, S.-K. Angew. Chem., Int. Ed. 2013, 52, 4929.
62. Su, Y.-H.; Wu, Z.; Tian, S.-K. Chem. Commun. 2013, 49, 6528.
63. Zhang, Y.-G.; Liu, X.-L.; He, Z.-Y.; Li, X.-M.; Kang, H.-J.; Tian, S.-K. Chem.-Eur. J. 2014, 20, 2765.
64. Yang, F.-L.; Wang, F.-X.; Wang, T.-T.; Wang, Y.-J.; Tian, S.-K. Chem. Commun. 2014, 50, 2111.
65. + 337.0981, found 337.0987.
66. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada. Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
67. Mäeorg, U.; Bredihhin, A. Org. Lett. 2007, 9, 4975.
68. Zhang, Z.; Wang, M.; Yao, X.; Li, Y.; Tan, J.; Wang, L.; Qiao, W.; Geng, Y.; Liu, Y.; Wang, Q. Eur. J. Med. Chem. 2012, 54, 33.