Effective and recyclable dendritic catalysts for the direct asymmetric Michael addition of aldehydes to nitrostyrenes

Tetrahedron Asymmetry

Volumn 17, Issue 13, 2006, Pages 2034-2039

  Li, Yawen ^a   Liu, Xin Yuan ^b   Zhao, Gang ^a,b  

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

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 TRIMETHYLSILANYLOXYMETHYLPYRROLIDINE; ALDEHYDE; PYRROLIDINE DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; DIASTEREOISOMER; ENANTIOSELECTIVITY; MICHAEL ADDITION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS;

EID: 33747002158     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.07.004     Document Type: Article

References (47)

1. Perlmutter P. Conjugate Addition Reactions in Organic Synthesis (1992), Pergamon, Oxford
2. For recent reviews of asymmetric Michael addition reactions, see:. Tomioka K., Nagaoka Y., and Yamaguchi M. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. III (1999), Springer, New York 1105-1139 Chapters 31.1 and 31.2
3. Krause N., and Hoffmann-Röder A. Synthesis (2001) 171
4. Christoffers J., and Baro A. Angew. Chem., Int. Ed. 42 (2003) 1688
5. Christoffers J., and Baro A. Angew. Chem. 115 (2003) 1726
6. Notz W., Tanaka F., and Barbas III C.F. Acc. Chem. Res. 37 (2004) 580
7. Li H.M., Wang Y., Tang L., and Deng L. J. Am. Chem. Soc. 126 (2004) 9906
8. Okino T., Hoashi Y., and Takemoto Y. J. Am. Chem. Soc. 125 (2003) 12672
9. Okino T., Hoashi Y., Furukawa T., Xu X., and Takemoto Y. J. Am. Chem. Soc. 127 (2005) 119
10. Cobb A.J.A., Longbottom D.A., Shaw D.M., and Ley S.V. Chem. Commun. (2004) 1808
11. Cobb A.J.A., Shaw D.M., Longbottom D.A., Gold J.B., and Ley S.V. Org. Biomol. Chem. 3 (2005) 84
12. Betancort J.M., and Barbas III C.F. Org. Lett. 3 (2001) 3737
13. Mase N., Thayumanavan R., Tanaka F., and Barbas III C.F. Org. Lett. 6 (2004) 2527
14. Betancort J.M., Sakthivel K., Thayumanavan R., Tanaka F., and Barbas III C.F. Synthesis (2004) 1509
15. Alexakis A., and Andrey O. Org. Lett. 4 (2002) 3611
16. Andrey O., Alexakis A., and Bernardinelli G. Org. Lett. 5 (2003) 2559
17. Andrey O., Alexakis A., Tomassini A., and Bernardinelli G. Adv. Synth. Catal. 346 (2004) 1147
18. Sakthivel K., Notz W., Bui T., and Barbas III C.F. J. Am. Chem. Soc. 123 (2001) 5260
19. List B., Pojarliev P., and Martin H.J. Org. Lett. 3 (2001) 2423
20. Terakado D., Takano M., and Oriyama T. Chem. Lett. 34 (2005) 962
21. Ishii T., Fujioka S., Sekiguchi Y., and Kotsuki H. J. Am. Chem. Soc. 126 (2004) 9558
22. Wang W., Wang J., and Li H. Angew. Chem., Int. Ed. 44 (2005) 1369
23. Hayashi Y., Gotoh H., Hayashi T., and Shoji M. Angew. Chem., Int. Ed. 44 (2005) 4212
24. For recent reviews on dendritic catalysts, see:. Oosterom G.E., Reek J.N.H., Kamer P.C.J., and van Leeuwen P.W.N.M. Angew. Chem., Int. Ed. 40 (2001) 1828
25. Astruc D., and Chardac F. Chem. Rev. 101 (2001) 2991
26. Crooks R.M., Zhao M., Sun L., Chechik V., and Yueng L.K. Acc. Chem. Res. 34 (2001) 181
27. Twyman L.J., King A.S.H., and Martin I.K. Chem. Soc. Rev. 31 (2002) 69
28. van Heerbeek R., Kamer P.C.J., van Leeuwen P.W.N.M., and Reek J.N.H. Chem. Rev. 102 (2002) 3717
29. Fan Q.-H., Li Y.-M., and Chan A.S.C. Chem. Rev. 102 (2002) 3385
30. Caminade A.M., Maraval V., Laurent R., and Majoral J.P. Curr. Org. Chem. 6 (2002) 739
31. For a review on the nanofiltration technique in dendritic catalyst recycling, see:. Dijkstra H.P., van Klink G.P.M., and van Koten G. Acc. Chem. Res. 35 (2002) 798
32. For selected reports on dendritic catalyst recycling by precipitation, see:. Reetz M.T., Lohmer G., and Schwickardi R. Angew. Chem., Int. Ed. 36 (1997) 1526
33. Petrucci-Samija M., Guillemette V., Dasgupta M., and Kakkar A.K. J. Am. Chem. Soc. 121 (1999) 1968
34. Hu Q.S., Pugh V., Sabat M., and Pu L. J. Org. Chem. 64 (1999) 7528
35. Fan Q.H., Chen Y.M., Chen X.M., Jiang D.Z., Xi F., and Chan A.S.C. Chem. Commun. (2000) 789
36. Maraval V., Laurent R., Caminade A.M., and Majoral J.P. Organometallics 19 (2000) 4025
37. Liu X.Y., Wu X.Y., Chai Z., Wu Y.Y., Zhao G., and Zhu S.Z. J. Org. Chem. 70 (2005) 7432
38. Wang G.Y., Liu X.Y., and Zhao G. Synlett (2006) 1150
39. Liu X.Y., Li Y.W., Wang G.Y., Chai Z., Wu Y.Y., and Zhao G. Tetrahedron: Asymmetry 17 (2006) 750
40. Seebach D., and Golinski J. Helv. Chim. Acta 64 (1981) 1413
41. Blarer S.J., Schweizer W.B., and Seebach D. Helv. Chim. Acta 65 (1982) 1637
42. Blarer S.J., and Seebach D. Chem. Ber. 116 (1983) 2250
43. Blarer S.J., and Seebach D. Chem. Ber. 116 (1983) 3086
44. Haner R., Laube T., and Seebach D. Chimia 38 (1984) 255
45. Seebach D., Beck A.K., Golinski J., Hay J.N., and Laube T. Helv. Chim. Acta 68 (1985) 162
46. Seebach D., and Brook M.A. Helv. Chim. Acta 68 (1985) 319
47. Seebach D., Missbach M., Calderari G., and Eberle M. J. Am. Chem. Soc. 112 (1990) 7625