Studies on palladium-catalyzed enantioselective cyclization of 3,4-allenylic hydrazines with organic halides

Tetrahedron

Volumn 64, Issue 49, 2008, Pages 11159-11166

  Shu, Wei ^a   Yang, Qing ^a,b   Jia, Guochen ^c   Ma, Shengming ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b JILIN UNIVERSITY   (China)

^c HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

Allenes; Cyclization; Enantioselectivity; Halides; Hydrazine

Indexed keywords

3,4 ALLENYLIC HYDRAZINE DERIVATIVE; HYDRAZINE DERIVATIVE; ORGANOHALOGEN DERIVATIVE; PALLADIUM; PYRAZOLE DERIVATIVE; PYRAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CYCLIZATION; ENANTIOSELECTIVITY; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 54549097927     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.049     Document Type: Article

References (69)

1. Khau V.V., and Martinelli M.J. Tetrahedron Lett. 37 (1996) 4323-4326
2. Hanessian S., McNaughton-Smith G., and Lombart H.G. Tetrahedron 53 (1997) 12789-12854
3. Kim H.O., Lum C., and Lee M.S. Tetrahedron Lett. 38 (1997) 4935-4938
4. Kutterer K.M.K., Davis J.M., Singh G., Yang Y., Hu W., Severin A., Rasmussen B.A., Krishnamurthy G., Faillic A., and Katzc A.H. Bioorg. Med. Chem. Lett. 15 (2005) 2527-2531
5. Ahn J.H., Kim J.A., Kim H.M., Kwon H.M., Huh S.C., Rhee S.D., Kim K.R., Yang S.D., Park S.D., Lee J.M., Kim S.S., and Cheon H.G. Bioorg. Med. Chem. Lett. 15 (2005) 1337-1340
6. Cheon H.G., Kim S.S., Kim K.R., Rhee S.D., Yang S.D., Ahn J.H., Park S.D., Lee J.M., Jung W.H., Lee H.S., and Kim H.Y. Biochem. Pharmacol. 70 (2005) 22-29
7. For some reviews, see:
8. Huisgen R., Grashey R., and Sauer J. In: Patai S. (Ed). The Chemistry of Alkenes: Cycloaddition Reactions of Alkenes (1964), Interscience, New York, NY 739-953
9. Huisgen R. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry: 1,3-Dipolar Cycloaddition-Introduction, Survey, Mechanism Vol. 1 (1984), Wiley-Interscience, New York, NY 1-176
10. Huisgen R. In: Curran D.P. (Ed). Advance in Cycloaddition: Steric Course and Mechanism of 1,3-Dipolar Cycloaddition Vol. 1 (1988), JAI, Greenwich, CT 1-31
11. Kobayashi S., Shimizu H., Yamashita Y., Ishitani H., and Kobayashi J. J. Am. Chem. Soc. 124 (2002) 13678-13679
12. Mish M.R., Guerra F.M., and Carreira E.M. J. Am. Chem. Soc. 119 (1997) 8379-8380
13. Gallos J.K., Koumbis A.E., and Apostolakis N.E. J. Chem. Soc., Perkin Trans. 1 (1997) 2457-2459
14. Kobayashi S., Hirabayashi R., Shimizu H., Ishitani H., and Yamashita Y. Tetrahedron Lett. 44 (2003) 3351-3354
15. Jäger V., Bierer L., Dong H.Q., Palmer A.M., Shaw D., and Frey W. J. Heterocycl. Chem. 37 (2000) 455-465
16. Ellis J.M., and King S.B. Tetrahedron Lett. 43 (2002) 5833-5835
17. Bonner W.A. In: Eliel E., and Wilen S.H. (Eds). Topics in Stereochemistry Vol. 18 (1988), John Wiley and Sons, New York, NY 1-96
18. For recent reports on synthesis of optically active pyrazolidines, see:
19. Guerra F.M., Mish M.R., and Carreira E.M. Org. Lett. 2 (2000) 4265-4267
20. Whitlock G.A., and Carreira E.M. Helv. Chim. Acta 83 (2000) 2007-2022
21. Barluenga J., Fernandez-Mari F., Viado A.L., Aguilar E., Olano B., Garcia-Granda S., and Moya-Rubiera C. Chem.-Eur. J. 5 (1999) 883-896
22. Stanovnik B., Jelen B., Turk C., Zlicar M., and Svete J. J. Heterocycl. Chem. 35 (1998) 1187-1204
23. Rutjes F.P.J.T., Teerhuis N.M., Hiemstra H., and Speckhamp W.N. Tetrahedron 49 (1993) 8605-8628
24. Chauveau A., Martens T., Bonin M., Micouin L., and Husson H.P. Synthesis (2002) 1885-1890
25. Yamashito Y., and Kobayashi S. J. Am. Chem. Soc. 126 (2004) 11279-11282
26. For recent reviews on transition metal-catalyzed reactions for synthesis of heterocyclic compounds, see:
27. Royer J., Bonin M., and Micouin L. Chem. Rev. 104 (2004) 2285-2310
28. Nakamura I., and Yamamoto Y. Chem. Rev. 104 (2004) 2127-2198
29. Deiters A., and Martin S.F. Chem. Rev. 104 (2004) 2199-2238
30. McReynolds M.D., Dougherty J.M., and Hanson P.R. Chem. Rev. 104 (2004) 2239-2258
31. For most recent reviews, see:
32. Krause N., and Hashmi A.S.K. Modern Allene Chemistry Vols. 1-2 (2004), Wiley-VCH, Weinheim, Germany
33. Ma S. Chem. Rev. 105 (2005) 2829-2872
34. Trost B.M., and Dietsche T.J. J. Am. Chem. Soc. 95 (1973) 8200-8201
35. Trost B.M., and Strege P.E. J. Am. Chem. Soc. 99 (1977) 1649-1651
36. Fiaud J.C., and Legros J.Y. J. Org. Chem. 55 (1990) 4840-4846
37. Yamaguchi M., Shima T., Yamagishi T., and Hida M. Tetrahedron: Asymmetry 2 (1991) 663-666
38. von Matt P., Loiseleur O., Koch G., Pfaltz A., Lefeber C., Feucht T., and Helmchen G. Tetrahedron: Asymmetry 5 (1994) 573-584
39. Trost B.M., and Bunt R.C. J. Am. Chem. Soc. 116 (1994) 4089-4090
40. Baldwin I.C., Williams J.M.J., and Beckett R.P. Tetrahedron: Asymmetry 6 (1995) 1515-1518
41. Trost B.M., and Van Vranken D.L. Chem. Rev. 96 (1996) 395-422
42. Yan X., Liang C., Zhang Y., and Hou X. Angew. Chem., Int. Ed. 44 (2005) 6544-6546
43. Zheng W., Zheng B., Zhang Y., and Hou X. J. Am. Chem. Soc. 129 (2007) 7718-7719
44. Jumnah R., Williams A.C., and Williams J.M.J. Synlett (1995) 821-822
45. Yamazaki A., and Achiwa K. Tetrahedron: Asymmetry 6 (1995) 51-54
46. Togni A., Burckhardt U., Gramlich V., Pregosin P.S., and Salzmann R. J. Am. Chem. Soc. 118 (1996) 1031-1037
47. Constantieux T., Brunel J.M., Labande A., and Buono G. Synlett (1998) 49-50
48. You S., Zhu X., Luo Y., Hou X., and Dai L. J. Am. Chem. Soc. 123 (2001) 7471-7472
49. Trost B.M., and Toste F.D. J. Am. Chem. Soc. 120 (1998) 815-816
50. Trost B.M., and Brennan M.K. Org. Lett. 9 (2007) 3961-3964
51. Eichelmann H., and Gais H.J. Tetrahedron: Asymmetry 6 (1995) 643-646
52. Trost B.M., Organ M.G., and O'Doherty G.A. J. Am. Chem. Soc. 117 (1995) 9662-9670
53. For recent reviews on asymmetric allyic alkylation:
54. Consiglio G., and Waymouth R.M. Chem. Rev. 89 (1989) 257-276
55. Trost B.M., and Crawley M.L. Chem. Rev. 103 (2003) 2921-2943
56. Lu Z., and Ma S. Angew. Chem., Int. Ed. 47 (2008) 258-297
57. Yamamoto K., and Tsuji J. Tetrahedron Lett. 23 (1982) 3089-3092
58. Genet J.P., and Grisoni S. Tetrahedron Lett. 29 (1988) 4543-4546
59. Takemoto T., Nishikimi Y., Sodeoka M., and Shibasaki M. Tetrahedron Lett. 33 (1992) 3531-3532
60. Larock R.C., and Zenner J.M. J. Org. Chem. 60 (1995) 482-483
61. Larock R.C., and Zenner J.M. J. Org. Chem. 64 (1999) 7312-7322
62. Ma S., Jiao N., Zheng Z., Ma Z., Lu Z., Ye L., Deng Y., and Chen G. Org. Lett. 6 (2004) 2193-2196
63. Yang Q., Jiang X., and Ma S. Chem.-Eur. J. 13 (2007) 9310-9316
64. For the synthesis of trioxazolines, see:
65. Zhou J., and Tang Y. J. Am. Chem. Soc. 124 (2002) 9030-9031
66. Zhou J., Ye M., Huang Z., and Tang Y. J. Org. Chem. 69 (2004) 1309-1320
67. Ye M., Li B., Zhou J., Sun X., and Tang Y. J. Org. Chem. 70 (2005) 6108-6110
68. Rasmussen L.K. J. Org. Chem. 71 (2006) 3627-3629 and reference therein
69. Poulsen T.B., Alemparte C., and Jørgensen K.A. J. Am. Chem. Soc. 127 (2005) 11614-11615