Solvent- and catalyst-free conjugate additions of organozinc to β-nitroalkene

Synlett

Volumn , Issue 14, 2007, Pages 2272-2276

  Huang, Danfeng ^a   Wang, Jin Xian ^a,b  

^a NORTHWEST NORMAL UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

Nitroalkenes; Allylzinc; Benzylzinc; Conjugate addition; Solvent free

Indexed keywords

ALKENE DERIVATIVE; BETA NITROALKENE; BROMIDE; ORGANOMETALLIC COMPOUND; STYRENE DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CATALYST; CHEMICAL REACTION; CONJUGATE; ROOM TEMPERATURE; SYNTHESIS;

EID: 34548772310     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985588     Document Type: Article

References (38)

1. (a) Perlmuter, P. In Conjugate Addition Reaction in Organic Synthesis, In Tetrahedron Organic Chemistry Series, No. 9; Pergamon Press: Oxford, 1992, 1.
2. (b) Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. In Stereoselective Synthesis. Houben-Weyl, Methods of Organic Chemistry, Vol. E21b, 4th ed.; Georg Thieme Verlag: Stuttgart, 1995, 1041.
3. (a) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.
4. (b) Knochel, P.; Prea, J. A.; Jones, P. Tetrahedron 1998, 54, 8275.
5. (a) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Chem. Soc. 2003, 125, 3700.
6. (b) Hird, A. W.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2003, 42, 1276.
7. (c) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362.
8. (d) Gallo, E.; Ragaini, F.; Licia, B.; Piarulli, U. J. Organomet. Chem. 2004, 689, 2169.
9. (e) Knopff, O.; Alexakis, A. Org. Lett. 2002, 4, 3835.
10. (f) Mampreian, D. M.; Hoveyda, A. D. Org. Lett. 2004, 6, 2829.
11. (g) Bräse, S.; Höfener, S. Angew. Chem. Int. Ed. 2005, 44, 7879.
12. (h) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
13. (a) Lipshutz, B. H.; Wood, M. R.; Tirado, R. J. Am. Chem. Soc. 1995, 11, 6126.
14. (b) Maezaki, N.; Sawamto, H.; Yoshigami, R.; Suzuki, T.; Tanaka, T. Org. Lett. 2003, 5, 1345.
15. (c) Yuguchi, M.; Tokuda, M.; Orito, K. Chem. Lett. 2004, 33, 674.
16. (d) Yuguchi, M.; Tokuda, M.; Orito, K. Bull. Chem. Soc. Jpn. 2004, 1031.
17. (a) Ongeri, S.; Piarulli, U.; Jackson, R. F. W.; Gennari, C. Eur. J. Org. Chem. 2001, 803.
18. (b) Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
19. (a) Namboothiri, I. N. N.; Hassner, A. J. Organomet. Chem. 1996, 518, 69.
20. (b) Yao, C.-F.; Kao, K.-H.; Liu, J.-T.; Chu, C.-M.; Wang, Y. Tetrahedron 1998, 54, 791.
21. Ashwood, M. S.; Bell, L. A.; Houghton, P. G.; Wright, S. H. B. Synthesis 1988, 379.
22. Knochel, P.; Seebach, D. Tetrahedron Lett. 1981, 22, 3223.
23. Pecunioso, A.; Menicagli, R. J. Org. Chem. 1988, 53, 45.
24. Zhang, J. M.; Zhang, Y. M. Chin. J. Chem. 2002, 20, 296.
25. Bao, W. L.; Zheng, Y. F.; Zhang, Y. M. J. Chem. Res., Synop. 1999, 732.
26. Kumar, H. M. S.; Reddy, B. V. S.; Reddy, P. T.; Yadav, J. S. Tetrahedron Lett. 1999, 40, 5387.
27. (a) Wang, J.-X.; Fu, Y.; Hu, Y. L. Angew. Chem. Int. Ed. 2002, 41, 2757.
28. (b) Wang, J.-X.; Wang, K.; Zhao, L.; Fu, Y.; Hu, Y. L. Adv. Synth. Catal. 2006, 348, 1262.
29. (c) Hu, Y. L.; Yu, J. H.; Yang, S.; Wang, J.-X. Synlett 1998, 1213.
30. (a) Hu, Y. L.; Yu, J. H.; Wang, J.-X.; Yin, Y. Q. Synth. Commun. 1998, 28, 2793.
31. (b) Hu, Y. L.; Yu, J. H.; Wang, J.-X.; Yin, Y. Q. Chin. Chem. Lett. 1998, 9, 699.
32. (c) Huang, D. F.; Yang, Y.; Wang, J.-X.; Hu, Y. L. J. Chem. Res., Synop. 2002, 79.
33. Wang, J.-X.; Jia, X. F.; Meng, T. J.; Xin, L. Synthesis 2005, 2838.
34. Menicagli, R.; Samaritani, S. Tetrahedron 1996, 52, 1425.
35. Berk, S. C.; Jeong, M. C. P. N.; Knochel, P. Organometallics 1990, 9, 3053.
36. 4 and concentrated. The pure product was obtained by column chromatography of the crude mixture on silica gel using PE-EtOAc as eluent.
37. 2: C, 69.09; H, 6.85; N, 7.32. Found: C, 68.46; H, 6.93; N, 6.57.
38. 3: C, 67.52; H, 5.67; N, 6.06. Found: C, 68.16; H, 5.27; N, 5.40.