Novel carbonyl allylation mediated by SnCl2/TiCl3 in water

Organic Letters

Volumn 5, Issue 11, 2003, Pages 1833-1835

  Tan, Xiang Hui ^a   Shen, Bo ^a   Beng, Wei ^a   Zhao, Hui ^a   Liu, Lei ^a,b   Guo, Qing Xiang ^a  

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

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL CHLORIDE; BROMIDE; CARBONYL DERIVATIVE; LEWIS ACID; STANNOUS CHLORIDE; TITANIUM DERIVATIVE;

ALLYLATION; ARTICLE; CATALYSIS; PRODUCTIVITY;

EID: 0141853112     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034267p     Document Type: Article

References (54)

1. (a) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997.
2. (b) Breslow, R. Acc. Chem. Res. 1991, 24, 159.
3. (c) Engberts, J. B. F. N.; Blandamer, M. J. Chem. Commun. 2001, 1701.
4. (d) Zhu, Z.-Q.; Zeng, J.-Q. Chin. J. Org. Chem. 2001, 21, 1095.
5. (e) Lindstroem, U. M. Chem. Rev. 2002, 102, 2751.
6. (a) Li, C. J. Chem. Rev. 1993, 93, 2023.
7. (b) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741.
8. (c) Li, C. J. Tetrahedron 1996, 52, 5643.
9. (d) Liao, L.-A.; Li, Z.-M. Chin. J. Org. Chem. 2000, 20, 306.
10. (e) Li, C. J. Green Chem. 2002, 4, 1.
11. Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736.
12. Zhang, W.-C.; Li, C.-J. J. Org. Chem. 1999, 64, 3230.
13. Li, C.-J.; Meng, Y.; Yi, X.-H.; Ma, J.; Chan, T.-H. J. Org. Chem. 1997, 62, 8632.
14. Kobayashi, S.; Aoyama, N.; Manabe, K. Synlett 2002, 483.
15. Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181.
16. (b) Cintas, P. Synlett 1995, 1087.
17. (c) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931.
18. (d) Chan, Y. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228.
19. (e) Loh, T. P.; Zhou, J. R.; Yin, Z. Org. Lett. 1999, 1, 1855.
20. (f) Yuan, Y.-F.; Cao, Z.; Hu, A.-G.; Wang, J.-T. Chin. J. Org. Chem. 2000, 20, 269.
21. (g) Hilt, G.; Smolko, K. I.; Waloch, C. Tetrahedron Lett. 2002, 43, 1437.
22. Li, L. H.; Chan, T. H. Tetrahedron Lett. 2000, 41, 5009.
23. (a) Wada, M.; Ohki, H.; Akiba, K. Y. Bull. Chem. Soc. Jpn. 1990, 63, 2751.
24. (b) Ren, P.-D.; Pan, S.-F.; Dong, T.-W.; Wu, S.-H. Chin. J. Chem. 1996, 14, 462.
25. Zhou, J.-Y.; Sun, G.-F.; Zhang, M.-F.; Jia, Y.; Wu, S.-H. Chin. J. Chem. 1997, 15, 361.
26. Wang, Z.; Yuan, S.; Li, C.-J. Tetrahedron Lett. 2002, 43, 5097.
27. (a) Pettier, C.; Luche, J. L. J. Org. Chem. 1985, 50, 910.
28. (b) Deng, D.; Lu, Z. Chin. Chem. Lett. 1994, 5, 173.
29. (c) Deng, D.-L.; Lu, Z.-H.; Wu, K. Chin. J. Org. Chem. 1996, 16, 462.
30. (d) Marton, D.; Stivanello, D.; Tagliavini, G. J. Org. Chem. 1996, 61, 2731.
31. (e) Yi, X. H.; Haberman, J. X.; Li, C. J. Synth. Commun. 1998, 28, 2999.
32. (a) Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 1527.
33. (b) Wu, S.; Zhu, T. Acta Chim. Sin. 1987, 45, 1135.
34. (c) Wu, S. H.; Huang, B. Z.; Zhu, T. M.; Yiao, D. Z.; Chu, Y. L. Acta Chim. Sin. 1990, 48, 372.
35. (d) Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452.
36. (e) Zou, C.-L.; Zha, Z.-G.; Wang, Z.-Y.; Wu, J.-H.; Zhang, J.-H. Chin. J. Chem. 2002, 20, 718.
37. (f) Zha, Z.-G.; Xie, Z.; Zhou, C.-L.; Wang, Z.-Y.; Wang, Y.-S. Chin. J. Chem. 2002, 20, 1477.
38. Okano, T.; Kiji, J.; Doi, T. Chem. Lett. 1998, 5.
39. Kundu, A.; Prabhakar, S.; Vairamani, M.; Roy, S. Organometallics 1997, 16, 4796.
40. Tan, X.-H.; Shen, B.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2002, 43, 9373.
41. 1H NMR without the need for further purification. If necessary (entries 6, 7, 11, 12, and 13), purification was performed by flash column chromatography over silica gel.
42. All the products were reported before in ref 16.
43. Ratio of dl:meso = 69:31 for allyl chloride. Ratio of dl:meso = 70:30 for allyl bromide.
44. 2 added in each of the five reactions are the same as mentioned in the typical procedure. McMurry, J. E. Chem. Rev. 1989, 89, 1513.
45. (a) Clerici, A.; Pastori, N.; Porta, O. Eur. J. Org. Chem. 2001, 2235.
46. (b) Clerici, A.; Pastori, N.; Porta, O. Eur. J. Org. Chem. 2002, 3326.
47. For recent studies on the electron-transfer reactions involving Ti(III), see: (a) Shey, J.; McGinley, C. M.; McCauley, K. M.; Dearth, A. S.; Young, B. T.; van der Donk, W. A. J. Org. Chem. 2002, 67, 837. (b) Barrero, A. F.; Oltra, J. E.; Cuerva, J. M.; Rosales, A. J. Org. Chem. 2002, 67, 2566. (c) Rana, K. J. ; Guin, C.; Roy, S. C. Tetrahedron Lett. 2000, 41, 9337.
48. For recent studies on the electron-transfer reactions involving Ti(III), see: (a) Shey, J.; McGinley, C. M.; McCauley, K. M.; Dearth, A. S.; Young, B. T.; van der Donk, W. A. J. Org. Chem. 2002, 67, 837. (b) Barrero, A. F.; Oltra, J. E.; Cuerva, J. M.; Rosales, A. J. Org. Chem. 2002, 67, 2566. (c) Rana, K. J. ; Guin, C.; Roy, S. C. Tetrahedron Lett. 2000, 41, 9337.
49. For recent studies on the electron-transfer reactions involving Ti(III), see: (a) Shey, J.; McGinley, C. M.; McCauley, K. M.; Dearth, A. S.; Young, B. T.; van der Donk, W. A. J. Org. Chem. 2002, 67, 837. (b) Barrero, A. F.; Oltra, J. E.; Cuerva, J. M.; Rosales, A. J. Org. Chem. 2002, 67, 2566. (c) Rana, K. J. ; Guin, C.; Roy, S. C. Tetrahedron Lett. 2000, 41, 9337.
50. For recent studies on organic reactions catalyzed by Lewis acids in water, see: (a) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209. (b) Li, H.-J.; Tian, H.-Y.; Chen, Y.-J.; Wang, D.; Li, C.-J. Chem. Commun. 2002, 2994. (c) Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 4719. (d) Rispens, T.; Engberts, J. B. F. N. Org. Lett. 2001, 3, 941.
51. For recent studies on organic reactions catalyzed by Lewis acids in water, see: (a) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209. (b) Li, H.-J.; Tian, H.-Y.; Chen, Y.-J.; Wang, D.; Li, C.-J. Chem. Commun. 2002, 2994. (c) Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 4719. (d) Rispens, T.; Engberts, J. B. F. N. Org. Lett. 2001, 3, 941.
52. For recent studies on organic reactions catalyzed by Lewis acids in water, see: (a) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209. (b) Li, H.-J.; Tian, H.-Y.; Chen, Y.-J.; Wang, D.; Li, C.-J. Chem. Commun. 2002, 2994. (c) Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 4719. (d) Rispens, T.; Engberts, J. B. F. N. Org. Lett. 2001, 3, 941.
53. For recent studies on organic reactions catalyzed by Lewis acids in water, see: (a) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209. (b) Li, H.-J.; Tian, H.-Y.; Chen, Y.-J.; Wang, D.; Li, C.-J. Chem. Commun. 2002, 2994. (c) Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 4719. (d) Rispens, T.; Engberts, J. B. F. N. Org. Lett. 2001, 3, 941.
54. Recently, Kobayashi et al. discovered that Cd(II) terpyridine complex can accelerate the allylation reactions between carbonyl compounds and allyltrimethoxysilane in aqueous media (Aoyama, N.; Hamada, T.; Manabe, K.; Kobayashi, S. Chem. Commun. 2003, 676). The mechanism of this reaction has not been clarified yet.