The solvent-free addition reaction of allylzinc bromide and carbony compounds

European Journal of Organic Chemistry

Volumn , Issue 18, 2009, Pages 2983-2986

  Zhang, Yumei ^a   Jia, Xuefeng ^a   Wang, Jin Xian ^a,b  

^a NORTHWEST NORMAL UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

Alcohols; Allylic compounds; Carbonyl compounds; Green chemistry; Zinc

Indexed keywords

EID: 66749164667     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900059     Document Type: Article

References (74)

1. a) Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207;
2. b) S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763;
3. c) K.-T. Tan, S.S. Chang, H.-S. Cheng, T-P. Loh, J. Am. Chem. Soc. 2003,125, 2958.
4. a) W-C Zhang, C-J. Li, J. Org. Chem. 1999, 64, 3230;
5. b) P. Jones, N. Millot, P. Knöchel, Chem. Commun. 1998, 2409;
6. c) P. Jones, P. Knöchel, Chem. Commun. 1998, 2407. .
7. R. Boati, V. Gouverneur, C Mioskowski, J. Org. Chem. 2000, 65, 1235.
8. T. Hirashita, S. Kambe, H. Tsuji, H. Omori, S. Araki, J. Org. Chem. 2004, 69, 5054.
9. H. Kakiya, S. Nishimae, H. Shinokubo, K. Oshima, Tetrahedron 2001, 57, 8807.
10. K.-H. Shen, C.-F. Yao, J. Org. Chem. 2006, 71, 3980.
11. a) J. S. Yadav, P. K. Chand, S. Anjaneyulu, Tetrahedron Lett. 2002, 43, 3783;
12. b) S. H. Kim, C Shin, A. N. Pae, H. Y. Koh, M. H. Chang, B. Y. Chang, Y. S. Cho, Synthesis 2004, 1581.
13. E-X. Felpin, M.-J. Bertrand, J. Lebreton, Tetrahedron 2002, 58, 7381.
14. a) B. M. Choudary, M. Roy, S. Roy, M. L. Kantam, K. Jyothi B. Sreedhar, Adv. Synth. Catal. 2005, 347, 2009;
15. b) B. Das, K. Laxminarayana, B. Ravikanth, B. Ramarao, Tetrahedron Lett. 2006, 47, 9103;
16. c) O. A. Wallner, K. J. Szabo, J. Org. Chem. 2003, 68, 2934.
17. E. Frankland, Justus Liebigs Ann. Chem. 1849, 71, 171.
18. E. Negishi, Ace. Chem. Res. 1982, 15, 340.
19. P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390.
20. P. Knochel, P. Jones, Organozinc Reagents. A Practical Approach, Oxford University Press, 1999.
21. a) S. C Berk, M. C. P. Yeh, N. Jeong, P. Knochel, Organometallics 1990, 9, 3053;
22. b) S. Berger, F. Langer, C. Lutz, P. Knochel, A. Mobley, C. K. Reddy, Angew. Chem. 1997, 109, 1603;
23. Angew. Chem. Int. Ed. Engl. 1997, 36, 1496;
24. c) M. Rottändler, P. Knöchel, Tetrahedron Lett. 1997, 38, 1749;
25. d) L. Zliu, R. M, Wehmeyer, R, D. Rieke, J. Org. Chem. 1991, 56, 1445.
26. a) F. Langer, J. Waas, P. Knochel, Tetrahedron Lett. 1993, 34, 5261;
27. b) F. Langer, L. Schwink, A. Devasagayaraj, P.-Y. Chavant, P. Knochel, J. Org. Chem. 1996, 61, 8229;
28. c) A. Boudier, E. Hupe, P. Knochel, Angew. Chem. 2000, 112, 2396;
29. Angew. Chem. Int. Ed. 2000, 39, 2294.
30. a) T. Sato, K. Soai, K. Suzuki, T. Mukaiyama, Chem. Lett. 1978, 601;
31. b) T. Mukaiyama, K. Soai, T. Sato, H. Shimizu, K. Suzuki, J. Am. Chem. Soc. 1979, 101, 1455.
32. a) E. Nakamura, S. Aoki, K. Sekiya, H. Oshino, I. Kuwajima, J. Am. Chem. Soc, 1987, 109, 8056;
33. b) L. Micouin, M, Oestreich, P. Knochel, Angew. Chem. 1997, 109, 274;
34. Angew. Chem. Int. Ed. Engl. 1997, 36, 245;
35. c) R. F. W. Jackson, D. Turner, M. H. Block, J. Chem. Soc. Perkin Trans. 1 1997, 865;
36. d) R, Rossi, F. Bellina, D. Ciucci, J. Organamet. Chem. 1997, 542, 113;
37. e) D. C. Jou, T Y Hsiao, M. Y Wu, K. C. Kong, C. H. Cheng, Tetrahedron 1998, 54, 1041.
38. a) K. Soai, S. Niwa, Chem. Rew. 1992, 92, 33;
39. b) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34;
40. Angew. Chem. Int. Ed. Engl. 1991, 30, 49;
41. c) A. Huí, J. Zhang, J. Fan, Z. Wang, Tetrahedron: Asymmetry 2006, 17, 2101;
42. d) M. Iiatano, T Miyamoto, K. Ishihara, Curr. Org. Chem. 2007, 77, 127.
43. a) P. Knöchel, J.J.A. Perea, P. Jones, 'Tetrahedron 1998, 54, 8275;
44. b) X. Men, K. Wang, J.-X. Wang, X. Shi, Chin. J. Org. Chem. 2004, 24, 825 (in Chinese).
45. a) E. Nakamura, S. Aoki, K, Sekiya, H. Oshino, I, Kuwajima, J. Am. Chem. Soc. 1987, 109, 8056;
46. b) P. Knöchel, R. D. Singer, Chem. Rev. 1993, 93, 2117;
47. c) R. Rossi, F. Bellina, D. I Ciucci, Organomet. Chem. 1997, 542, 113;
48. d) D. C Jou, TY Hsiao, M. Y. Wu, K, C. Kong, C. H. Cheng, Tetrahedron 1998, 54, 1041.
49. Y. Hu, J. Yu, S. Yang, J.-X. Wang, Y. Yin, Synth. Commun. 1998, 28, 2793.
50. Y. Hu, I Yu, S. Yang, J.-X. Wang, Y. Yin, Synlett 1998, 1213.
51. M. C Law, K. Y. Wong, T. H. Chan, J. Org. Chem. 2005, 70, 10434.
52. N. Kuroiio, T. Inoue, M. Tokuda, Tetrahedron 2005, 61, 11125.
53. a) J.-X. Wang, Y. Fu, Y. Hu, Angew. Chem. 2002, 114, 4344;
54. Angew. Chem. Int. Ed. 2002, 41, 2757;
55. b) J.-X. Wang, Y. Fu, Y. Hu, K. Wang, Synthesis 2003, 1506;
56. c) J.-X. Wang, K. Wang, L. Zhao, H. Li, Y. Fu, Y. Hu, Adv. Synth. Catal. 2006, 348, 1262.
57. a) K. Tanaka, F. Toda, Chem. Rev. 2000, 100, 1025;
58. b) K. Tanaka, Solvent-Free Organic Synthesis, Wiley-VCH, Weinheim, Germany, 2003.
59. M. Yasuda, T. A. Fujibayashi, A. Baba, J. Org. Chem. 1998, 63, 6401.
60. a) X.-H. Tan, Y-Q. Hou, C Huang, L. Liu, Q.-X. Guo, Tetrahedron 2004, 60, 6129;
61. b) X.-H. Tan, Y-Q. Hou, L. Liu, Q.-X. Guo, Chin. J. Chem. 2004, 22, 450.
62. P. Gomes, C, Gosmini, J. Perichon, Synthesis 2003, 1909.
63. H. Schumann, J. Kaufmann, S. Dechert, H.-G. Schmalz, Tetrahedron Lett. 2002, 43, 3507.
64. T-S. Jang, G. Keum, S. B. Kang, B. Y. Chung, Y. Kim, Synthe- lpsis 2003, 775.
65. M. Riediker, R. O. Duthaler, Angew. Chem. 1989, 101, 488;
66. Angew. Chem. Int. Ed. Engl. 1989, 28, 494.
67. T. Nagase, K. Seike, K. Shiraishi, Y. Yamada, S. Ozaki, Chem. Lett. 1988, 2049.
68. C J. Kowaski, J.-S. Dung, J. Am. Chem. Soc. 1980, 102, 7950.
69. Y. Yamamoto, H. Yatagai, Y. Ishihara, N. Maeda, K. Maruyama, Tetrahedron 1984, 40, 2239.
70. H. Doucet, M. Santelli, Tetrahedron: Asymmetry 2000, 113, 4163.
71. G. Daudé, M. Pereyre, J. Organomet. Chem. 1980, 7.90, 43.
72. Y Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207.
73. R. Hamasaki, Y Chounan, H. Horino, Y. Yamamoto, Tetrahedron Lett. 2000, 41, 9883.
74. A. I Pearson, T. R, Perrior, J. Organomet. Chem. 1985, 285, 253.