Enantioselective Michael addition of malonate esters to nitroolefins organocatalyzed by diaryl-2-pyrrolidinemethanols

Tetrahedron Asymmetry

Volumn 17, Issue 5, 2006, Pages 837-841

  Lattanzi, Alessandra ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ESTER DERIVATIVE; MALONIC ACID DERIVATIVE; METHANOL DERIVATIVE; PROLINE; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; MICHAEL ADDITION; PRIORITY JOURNAL; QUANTUM YIELD;

EID: 33645775790     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.02.024     Document Type: Article

References (38)

1. For a recent review, see:. Berner O.M., Tedeschi L., and Enders D. Eur. J. Org. Chem. (2002) 1877
2. Ono N. The Nitro Group in Organic Synthesis (2001), Wiley-VCH, Weinheim, Germany
3. Ji J., Barnes D.M., Zhang J., King S.A., Wittenberger S.J., and Morton H.E. J. Am. Chem. Soc. 121 (1999) 10215
4. Barnes D.M., Ji J., Fickes M.G., Fitzgerald M.A., King S.A., Morton H.E., Plagge F.A., Preskill M., Wagan S.H., Wittenberger S.J., and Zhang J. J. Am. Chem. Soc. 124 (2002) 13097
5. Alexakis A., Benhaim C., Rosset S., and Humam M. J. Am. Chem. Soc. 124 (2002) 5262
6. Luchaco-Cullis C.A., and Hoveyda A.H. J. Am. Chem. Soc. 124 (2002) 8192
7. Duursma A., Minnaard A.J., and Feringa B.L. J. Am. Chem. Soc. 125 (2003) 3700
8. Watanabe M., Ikagawa A., Wang H., Murata K., and Ikariya T. J. Am. Chem. Soc. 126 (2004) 11148
9. Evans D.A., and Seidel D. J. Am. Chem. Soc. 127 (2005) 9958
10. List B., Pojarliev P., and Martin H.J. Org. Lett. 3 (2001) 2423
11. Bentacort J.M., and Barbas III C.F. Org. Lett. 3 (2001) 3737
12. Enders D., and Seki A. Synlett (2002) 26
13. Andrey O., Alexakis A., and Belardinelli G. Org. Lett. 5 (2003) 2559
14. Mase N., Thayumanavan R., Tanaka F., and Barbas III C.F. Org. Lett. 6 (2004) 2527
15. Ishii T., Fujioka S., Sekiguchi Y., and Kotsuki H. J. Am. Chem. Soc. 126 (2004) 9558
16. Cobb A.J.A., Longbottom D.A., Shaw D.M., and Ley S.V. Chem. Commun. (2004) 1808
17. Bentacort J.M., Sakthivel K., Thayumanavan R., Tanaka F., and Barbas III C.F. Synthesis (2004) 1509
18. Wang W., Wang J., and Li H. Angew. Chem., Int. Ed. 44 (2005) 1369
19. Hayashi Y., Gotoh H., Hayashi T., and Shoji M. Angew. Chem., Int. Ed. 44 (2005) 4212
20. Mitchell C.E.T., Cobb A.J.A., and Ley S.V. Synlett (2005) 611
21. Knudsen K.R., Mitchell C.E.T., and Ley S.V. Chem. Commun. (2006) 66
22. Blarer S.J., and Seebach D. Chem. Ber. 116 (1983) 2250
23. Okino T., Hoashi Y., and Takemoto Y. J. Am. Chem. Soc. 125 (2003) 12672
24. Okino T., Hoashi Y., Fururkawa T., Xu X., and Takemoto Y. J. Am. Chem. Soc. 127 (2005) 119
25. Wang J., Li H., Duan W., Zu L., and Wang W. Org. Lett. 7 (2005) 4713
26. Li H., Wang Y., Tang L., and Deng L. J. Am. Chem. Soc. 126 (2004) 9906
27. Li H., Wang Y., Tang L., Wu F., Liu X., Guo C., Foxman B.M., and Deng L. Angew. Chem., Int. Ed. 44 (2005) 105
28. Ye J., Dixon D.J., and Hynes P.S. Chem. Commun. (2005) 4481
29. McCooey S.H., and Connon S.J. Angew. Chem., Int. Ed. 44 (2005) 6367
30. Lattanzi A. Org. Lett. 7 (2005) 2579
31. Lattanzi A. Adv. Synth. Catal. 348 (2006) 339
32. Catalysts 1d-h have been reported previously and were synthesized according to the following literature procedures:. Mature D.J., Jones T.K., Xavier L.C., Blacklock T.J., Reamer R.A., Mohan J.J., Turner Jones E.T.T., Hoogsteen K., Baum M.W., and Grabowski E.J.J. J. Org. Chem. 56 (1991) 751
33. Bailey D., O'Hagan D., and Tavash M. Tetrahedron: Asymmetry 8 (1997) 149
34. Electron-donating groups on the benzene ring of the catalysts increase amine basicity by means of inductive or electronic effects.
35. These results point out that the double activation does not exclusively pertain to enantiomerically pure thioureas and chincona derivatives. For examples on bifunctional catalysis in Michael addition mediated by tertiary amines derived from cinchona derivatives, see:. Hermann K., and Wynberg H. J. Org. Chem. 44 (1979) 2238
36. Latvala A., Stanchev S., Linden A., and Hesse M. Tetrahedron: Asymmetry 4 (1993) 173
37. For recent reviews on organocatalysis, see:. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5183
38. Seayad J., and List B. Org. Biomol. Chem. 3 (2005) 719