Chiral phosphoric acid catalyzed enantioselective allylation of aldehydes with allyltrichlorosilane

Chinese Journal of Chemistry

Volumn 29, Issue 8, 2011, Pages 1669-1671

  Cheng, Ke ^a,b   Fan, Tiantian ^a   Sun, Jian ^a  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

aldehydes; allylation; allyltrichlorosilane; phosphoric acid

Indexed keywords

EID: 80052174925     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201180244     Document Type: Article

References (44)

1. Denmark, S. E.,;, Almstead, N. G., In Modern Carbonyl Chemistry, Ed.:, Otera, J., Wiley-VCH, Weinheim, 2000, h10, pp. 299-402.
2. Chemler, S. R.,;, Roush, W. R., In Modern Carbonyl Chemistry, Ed.:, Otera, J., Wiley-VCH, Weinheim, 2000, 11, pp. 403-490.
3. Yamamoto, Y.,;, Asao, N.,. Chem. Rev., 1993, 93, 2207.
4. Helmchen, G.,;, Hoffmann, R.,;, Mulzer, J.,;, Schaumann, E., In Stereoselective Synthesis Methods of Organic Chemistry (Houben-Weyl), Vol. 3, 21 st ed., Thieme Stuttgart, New York, 1996, pp. 1357-1602.
5. Denmark, S. E.,;, Fu, J.,. Chem. Rev., 2003, 103, 2763.
6. Denmark, S. E.,;, Coe, D. M.,;, Pratt, N. E.,;, Griedel, B. D.,. J. Org. Chem., 1994, 59, 6161.
7. Iseki, K.,;, Kuroki, Y.,;, Takahashi, M.,;, Kishimoto, S.,;, Kobayashi, Y.,. Tetrahedron, 1997, 53, 3513.
8. Wadamoto, M.,;, Ozasa, N.,;, Yanagisawa, A.,;, Yamamoto, H.,. J. Org. Chem., 2003, 63, 5593.
9. Denmark, S. E.,;, Fu, J.,. J. Am. Chem. Soc., 2000, 122, 12021.
10. Denmark, S. E.,;, Fu, J.,. J. Am. Chem. Soc., 2001, 123, 9488.
11. Denmark, S. E.,;, Fu, J.,. Org. Lett., 2002, 4, 1951.
12. Denmark, S. E.,;, Fu, J.,;, Coe, D. M.,;, Su, X.,;, Pratt, N. E.,;, Griedel, B. D.,. J. Org. Chem., 2006, 71, 1513.
13. Denmark, S. E.,;, Pham, S. M.,;, Stavenger, R. A.,;, Su, X.,;, Wong, K.-T.,;, Nishigaichi, Y.,. J. Org. Chem., 2006, 71, 3904.
14. Hellwig, J.,;, Belser, T.,;, Müller, J. F. K.,. Tetrahedron Lett., 2001, 42, 5417.
15. Kobayashi, S.,;, Nishio, K.,. Tetrahedron Lett., 1993, 34, 3453.
16. Kobayashi, S.,;, Nishio, K.,. J. Org. Chem., 1994, 59, 6620.
17. Kobayashi, S.,;, Nishio, K.,. Synthesis, 1994, 457.
18. Iseki, K.,;, Mizuno, S.,;, Kurki, Y.,;, Kobayashi, Y.,. Tetrahedron Lett., 1998, 39, 2767.
19. Iseki, K.,;, Mizuno, S.,;, Kurki, Y.,;, Kobayashi, Y.,. Tetrahedron, 1999, 55, 977.
20. Malkov, A. V.,;, Mariani, A.,;, MacDougall, K. N.,;, Koè ovský, P.,. Org. Lett., 2004, 6, 2253.
21. Kobayashi, S.,;, Nishio, K.,. Chem. Lett., 1994, 1773.
22. Nakajima, M.,;, Saito, M.,;, Shiro, M.,;, Hashimoto, S.,. J. Am. Chem. Soc., 1998, 120, 6419.
23. Nakajima, M.,;, Saito, M.,;, Shiro, M.,;, Hashimoto, S.,. Chem. Pharm. Bull., 2000, 48, 306.
24. Shimada, T.,;, Kina, A.,;, Ikeda, S.,;, Hayashi, T.,. Org. Lett., 2002, 4, 2799.
25. Shimada, T.,;, Kina, A.,;, Hayashi, T.,. J. Org. Chem., 2003, 68, 6329.
26. Kina, A.,;, Shimada, T.,;, Hayashi, T.,. Adv. Synth. Catal., 2004, 346, 1169.
27. Traverse, J. F.,;, Zhao, Y.,;, Hoveyda, A. H.,;, Snapper, M. L.,. Org. Lett., 2005, 7, 3151.
28. Hrdina, R.,;, Valterová, I.,;, Hodaèová, J.,;, Císaøová, I.,;, Kotora, M.,. Adv. Synth. Catal., 2007, 349, 822.
29. Malkov, A. V.,;, Orsini, M.,;, Pernazza, D.,;, Muir, K. W.,;, Langer, V.,;, Meghani, P.,;, Koèovský, P.,. Org. Lett., 2002, 4, 1047.
30. Malkov, A. V.,;, Bell, M.,;, Orsini, M.,;, Pernazza, D.,;, Massa, A.,;, Herrmann, P.,;, Meghani, P.,;, Koèovský, P.,. J. Org. Chem., 2003, 68, 9659.
31. Malkov, A. V.,;, Bell, M.,;, Vassieu, M.,;, Bugatti, V.,;, Koèovský, P.,. J. Mol. Catal. A, 2003, 196, 179.
32. Malkov, A. V.,;, Bell, M.,;, Castelluzzo, F.,;, Koèovský, P.,. Org. Lett., 2005, 7, 3219.
33. Malkov, A. V.,;, Dufková, L.,;, Farrugia, L.,;, Koèovský, P.,. Angew. Chem., Int. Ed., 2003, 42, 3674.
34. Malkov, A. V.,;, Ramírez-López, P.,;, Biedermannová (nèeBendová), L.,;, Rulíšek, L.,;, Dufková, L.,;, Kotora, M.,;, Zhu, F.,;, Koèovský, P.,. J. Am. Chem. Soc., 2008, 130, 5341.
35. Taylor, M. S.,;, Jacobsen, E. N.,. Angew. Chem., Int. Ed., 2006, 45, 1520.
36. Connon, S. J.,. Angew. Chem., Int. Ed., 2006, 45, 3909.
37. Akiyama, T.,;, Itoh, J.,;, Fuchibe, K.,. Adv. Synth. Catal., 2006, 348, 999.
38. Rowlands, G. J.,;, Barnes, W. K.,. Chem. Commun., 2003, 2712.
39. Massa, A.,;, Capozzolo, L.,;, Scettri, A.,. Cent. Eur. J. Chem., 2010, 8, 1210.
40. Massa, A.,;, Malkov, A. V.,;, Koèovský, P.,;, Scettri, A.,. Tetrahedron Lett., 2003, 44, 7179.
41. Kobayashi, S.,;, Ogana, C.,;, Konishi, H.,;, Sugiura, M.,. J. Am. Chem. Soc., 2003, 125, 6610.
42. Akiyama, T.,. Chem. Rev., 2007, 107, 5744.
43. Terada, M.,. Chem. Commun., 2008, 4097.
44. Terada, M.,. Synthesis, 2010, 1929.