Copper(I{cyrillic, ukrainian}) hexafluorophosphate: a dual functional catalyst for three-component reactions of methyl phenyldiazoacetate with alcohols and aldehydes or α-ketoesters

Tetrahedron Letters

Volumn 49, Issue 48, 2008, Pages 6862-6865

  Yue, Yongli ^a,b,c   Guo, Xin ^a   Chen, Zhiyong ^b,c   Yang, Liping ^a   Hu, Wenhao ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE; COPPER HEXAFLUOROPHOSPHATE; ESTER DERIVATIVE; FLUOROPHOSPHATE; METHYLPHENYLDIAZOACETATE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 53549135456     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.090     Document Type: Article

References (50)

1. Padwa A., and Weingarten M.D. Chem. Rev. 96 (1996) 223
2. Doyle M.P., Mckervey M.A., and Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds (1998), John Wiley and Sons, New York
3. Lu C.D., Chen Z.Y., Liu H., Hu W.H., Mi A.Q., and Doyle M.P. J. Org. Chem. 69 (2004) 4856
4. Maryanoff B.E., and Retiz A.B. Chem. Rev. 89 (1989) 863
5. Aggarwal V.K., Fulton J.R., Sheldon C.G., and Vicente J.D. J. Am. Chem. Soc. 125 (2003) 6034
6. Mori T., Sawada Y., and Oku A. J. Org. Chem. 65 (2000) 3620
7. Reddy L.R., Gais H.J., Woo C.W., and Raabe G. J. Am. Chem. Soc. 124 (2002) 10427
8. Aggarwal V.K., and Richardson J. Chem. Commun. (2003) 2644
9. Aggarwal V.K., and Vasse J.L. Org. Lett. 5 (2003) 3987
10. Doyle M.P., Tamblvn W.H., and Bagheri V. J. Org. Chem. 46 (1981) 5094
11. Vanecko J.A., and West F.G. Org. Lett. 4 (2002) 2813
12. Pirrung M.P., and Werner J.A. J. Am. Chem. Soc. 108 (1986) 6060
13. Padwa A., Hornbuckle S.F., Fryxell G.E., and Stull P.D. J. Org. Chem. 54 (1989) 817
14. West F.G., Eberlein T.H., and Tester R.W. J. Chem. Soc., Perkin Trans. 1 (1993) 2857
15. Tester R.W., and West F.G. Tetrahedron Lett. 39 (1998) 4631
16. Clark J.S. Tetrahedron Lett. 33 (1992) 6193
17. Clark J.S., Dossetter A.G., Blake A.J., Whittingham W.S., and Li W.G. Chem. Commun. (1999) 749
18. Clark J.S., Bate A.L., and Grinter T. Chem. Commun. (2001) 459
19. Clark J.S., Whitlock G., Jiang S., and Onyia N. Chem. Commun. (2003) 2578
20. Clark J.S., Fessard T.S., and Wilson C. Org. Lett. 6 (2004) 1773
21. Eberlein T.H., West F.G., and Tester R.W. J. Org. Chem. 57 (1992) 3479
22. West F.G., Naidu B.N., and Tester R.W. J. Org. Chem. 59 (1994) 6892
23. Marmsater F.P., and West F.G. J. Am. Chem. Soc. 123 (2001) 5144
24. Marmsater F.P., Vanecko J.A., and West F.G. Tetrahedron 58 (2002) 2027
25. Marmsater F.P., Murphy G.K., and West F.G. J. Am. Chem. Soc. 125 (2003) 14724
26. Lu C.D., liu H., Chen Z.Y., Hu W.H., and Mi A.Q. Org. Lett. 7 (2005) 83
27. Huang H.X., Guo X., and Hu W.H. Angew. Chem., Int. Ed. 46 (2007) 1337
28. Hu, W. H.; Xu, X. F.; Zhou, J.; Liu, W. J.; Hu, J.; Yang, L. P.; Gong, L. Z. J. Am. Chem. Soc, 2008, ASAP.
29. Lu C.D., liu H., Chen Z.Y., Hu W.H., and Mi A.Q. Chem. Commun. (2005) 2624
30. Evans D.A., woerpel K.A., Hinman M.M., and Faul M.M. J. Am. Chem. Soc. 113 (1991) 726
31. Hansen K.B., Finney N.S., and Jacobsen E.N. Angew. Chem., Int. Ed. Engl. 34 (1995) 676
32. Pqrez P.J., Brookhart M., and Templeton J.L. Organometallics 12 (1993) 261
33. Kirmse W. Angew. Chem., Int. Ed. 42 (2003) 1088
34. Doyle M.P., Yan M., and Hu W.H. J. Am. Chem. Soc. 125 (2003) 4692
35. Thomas C.M., and Fu G.C. J. Am. Chem. Soc. 128 (2006) 4594
36. Yue Y.L., Wang Y.H., and Hu W.H. Tetrahedron Lett. 48 (2007) 3975
37. Seebach D. In: Scheffold R. (Ed). Modern Synthetic Method (1980), Otto Salle, Frankfurt
38. Kitamura M., Suga S., Kawai K., and Noyori R. J. Am. Chem. Soc. 108 (1986) 6071
39. Shibasaki M., Nishikimi Y., Iimori T., and Sodeoka M. J. Org. Chem. 108 (1989) 3354
40. Evans D.A., Kozlowski M.C., Burgey S.C., and MacMillan D.W.C. J. Am. Chem. Soc. 119 (1998) 7893
41. Grover P.T., Bhongle N.N., Wald S.A., and Senanayake C.H. J. Org. Chem. 65 (2000) 6283
42. Kubas G.J. Inorg. Synth. 19 (1979) 90
43. Doyle M.P., Peterson C.S., and Parker D.L. Angew. Chem., Int. Ed. 35 (1996) 1334
44. Doyle M.P., Peterson C.S., Protopopova M.N., and Marnett A.B. J. Am. Chem. Soc. 119 (1997) 8826
45. Doyle M.P., Peterson C.S., Zhou Q.L., and Nishiyama H. Chem, Commun. 2 (1997) 211
46. Doyle M.P., Chapman B.J., and Hu W.H. Org. Lett. 1 (1999) 1327
47. Doyle M.P., and Hu W.H. J. Org. Chem. 65 (2000) 8839
48. Doyle M.P., Hu W.H., Chapman B., and Marnett A.B. J. Am. Chem. Soc. 122 (2000) 5718
49. 1H NMR analysis for the determination of product ratio and diastereoselectivities. The crude product was further purified by column chromatography on silica gel using EtOAc-light petroleum as eluents to give desired products.
50. -3.