High regio- and stereoselective Barbier reaction of carbonyl compounds mediated by NaBF4/Zn (Sn) in water

New Journal of Chemistry

Volumn 27, Issue 9, 2003, Pages 1297-1300

  Zha, Zhenggen ^a   Xie, Zhen ^a   Zhou, Cunliu ^a   Chang, Mingxin ^a   Wang, Zhiyong ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

BORON; CARBONYL DERIVATIVE; FLUORINE; SODIUM; WATER; ZINC;

ADDITION REACTION; ALLYLATION; ARTICLE; CALCULATION; CHEMICAL ANALYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0142218325     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b303187j     Document Type: Article

References (39)

1. Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207.
2. (a) P. Sinha and S. Roy, Chem. Commun., 2001, 1798;
3. (b) C. J. Li and T. H. Chan, Organic Reactions in Aqueous Media, John Wiley & Sons, New York, 1997;
4. (c) C. J. Li, Tetrahedron, 1996, 52, 5643;
5. (d) A. Lubineau, J. Augé and Y. Queneau, Synthesis, 1994, 741;
6. (e) C. J. Li, Chem. Rev., 1993, 93, 2023.
7. (a) Z. Y. Wang, S. Z. Yuan and C. J. Li, Tetrahedron Lett., 2002, 43, 5097;
8. (b) W. C. Zhang and C. J. Li, J. Org. Chem., 1999, 64, 3230;
9. (c) C. J. Li and T. H. Chan, Tetrahedron, 1999, 55, 11 149;
10. (d) C. J. Li and W. C. Zhang, J. Am. Chem. Soc., 1998, 120, 9102;
11. (e) C. J. Li, Y. Meng, X. H. Yi, J. H. Ma and T. H. Chan, J. Org. Chem., 1998, 63, 7498;
12. (f) C. J. Li, Y. Meng, X. H. Yi, J. H. Ma and T. H. Chan, J. Org. Chem., 1997, 62, 8632;
13. (g) M. Wada, H. Ohki and K. Y. Akiba, Bull. Chem. Soc. Jpn., 1990, 63, 2751;
14. (h) M. Wada, H. Ohki and K. Y. Akiba, J. Chem. Soc., Chem. Commun., 1987, 708;
15. (i) K. Uneyama, N. Kamaki, A. Moriya and S. Torii, J. Org. Chem., 1985, 50, 5396;
16. (j) J. Nokami, S. Wakabayashi and R. Okawara, Chem. Lett., 1984, 869;
17. (k) C. Petrier and J. L. Luche, J. Org. Chem., 1983, 50, 910;
18. (l) J. Nokami, J. Otera, T. Sudo and R. Okawara, Organometallics, 1983, 2, 191.
19. (a) C. L. Zhou, Z. G. Zha and Z. Y. Wang, Chin. J. Chem., 2002, 20, 718;
20. (b) D. Marton, D. Stivanello and G. Tagliavini, J. Org. Chem., 1996, 61, 2731;
21. (c) S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 1989, 54, 3087;
22. (d) C. Einhorn and J. L. Luche, J. Organomet. Chem., 1987, 322, 177.
23. (a) B. Alcaide, P. Almendros, C. Aragoncillo and R. Rodrìguez- Acebes, J. Org. Chem., 2001, 66, 5208;
24. (b) T. H. Chen, Y. Yang and C. J. Li, J. Org. Chem., 1999, 64, 4452.
25. (a) X. H. Tan, B. Shen, L. Liu and Q. X. Guo, Tetrahedron Lett., 2002, 43, 9373;
26. (b) L. H. Li and T. H. Chen, Tetrahedron Lett., 2000, 41, 5009;
27. (c) L. H. Li and T. H. Chan, Org. Lett., 2000, 2, 1129;
28. (d) P. D. Ren, Q. H. Jin and Z. P. Yao, Synth. Commun., 1997, 27, 2761;
29. (e) A. Kundu, S. Prabhakar, M. Vairamani and S. Roy, Organometallics, 1997, 16, 4796;
30. (f) W. Wang, L. Shi and Y. Huang, Tetrahedron, 1990, 46, 3315.
31. Z. Y. Wang, Z. G. Zha and C. L. Zhou, Org. Lett., 2002, 4, 1683.
32. (a) T. P. Loh, K. T. Tan, J. Y. Yang and C. L. Xiang, Tetrahedron Lett., 2001, 42, 8701;
33. (b) R. Gewald, M. Kira and H. Sakurai, Synthesis, 1996, 111;
34. (c) K. Mikami, Y. Kimura, N. Kishi and T. Nakai, J. Org. Chem., 1983, 48, 281.
35. (a) Z. G. Zha, Z. Xie, C. L. Zhou, Z. Y. Wang and Y. S. Wang, Chin. J. Chem., 2002, 20, 1477;
36. (b) Z. G. Zha, Y. S. Wang, G. Yang, L. Zhang and Z. Y. Wang, Green Chem., 2002, 4, 578.
37. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian 98, Revision A.11, Gaussian Inc., Pittsburgh, PA, 1998.
38. J. M. Blackwell, W. E. Piers and R. McDonald, J. Am. Chem. Soc., 2002, 124, 1295.