l-Prolinol as a highly enantioselective catalyst for Michael addition of cyclohexanone to nitroolefins

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 14, 2009, Pages 3915-3918

  Chua, Pei Juan ^a   Tan, Bin ^a   Zeng, Xiaofei ^a   Zhong, Guofu ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

Asymmetric Michael addition; Cyclohexanone; Nitroolefin; Organocatalytic; Prolinol catalysis

Indexed keywords

ALKENE DERIVATIVE; CYCLOHEXANONE; PROLINE DERIVATIVE; PROLINOL; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; DIASTEREOISOMER; ENANTIOSELECTIVITY; MICHAEL ADDITION; REACTION ANALYSIS;

ALKENES; BENZOIC ACID; CATALYSIS; CYCLOHEXANONES; PYRROLIDINES; STEREOISOMERISM; TEMPERATURE;

EID: 67649639592     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.03.076     Document Type: Article

References (49)

1. Seayad J., and List B. Org. Biomol. Chem. 3 (2005) 719
2. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138
3. Fustero S., Moscardo J., Jimenez D., Peerez-Carrion M.D., Sanchez-Rosesllo M., and del Pozo C. Chem.- Eur. J. 14 (2008) 9868
4. de Figueiredo R.M., and Christmann M. Eur. J. Org. Chem. 16 (2007) 2575
5. Zu L., Xie H., Li H., Wang J., and Wang W. Adv. Synth. Catal. 349 (2007) 2660
6. Perlmutter P. Conjugate Addition Reactions in Organic Synthesis (1992), Pergamon, Oxford
7. Christoffers J., and Baro A. Angew. Chem., Int. Ed. 42 (2003) 1688
8. Berner O.M., Tedeschi L., and Enders D. Eur. J. Org. Chem. (2002) 1877
9. 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
10. Tan B., Chua P.J., Zeng X., Lu M., and Zhong G. Org. Lett. 10 (2008) 3489
11. Tan B., Shi Z., Chua P.J., and Zhong G. Org. Lett. 10 (2008) 3425
12. Tan B., Chua P.J., Li Y., and Zhong G. Org. Lett. 10 (2008) 2437
13. Zhu M.-K., Cun L.-F., Mi A.-Q., Jiang Y.-Z., and Gong L.-Z. Tetrahedron: Asymmetry 17 (2006) 491
14. Cao C.-L., Ye M.-C., Sun X.-L., and Tang Y. Org. Lett. 8 (2006) 2901
15. Mitchell C.E.T., Cobb A.J.A., and Ley S.V. Synlett (2005) 611
16. Ishii T., Fujioka S., Sekiguchi Y., and Kotsuki H. J. Am. Chem. Soc. 126 (2004) 9558
17. Cobb A.J.A., Longbottom D.A., Shaw M.D., and Ley S.V. Chem. Commun. (2004) 1808
18. Enders D., Huttl M.R.M., Grondal C., and Raabe G. Nature 441 (2006) 861
19. Palomo C., Vera S., Mielgo A., and Gomez-Bengoa E. Angew. Chem., Int. Ed. 45 (2006) 5984
20. Wang W., Wang J., and Li H. Angew. Chem., Int. Ed. 44 (2005) 1369
21. Hayashi Y., Gotoh H., Hayashi T., and Shoji M. Angew. Chem., Int. Ed. 44 (2005) 4212
22. Mase N., Thayumanavan R., Tanaka F., and Barbas III C.F. Org. Lett. 6 (2004) 2527
23. Ono N. The Nitro Group in Organic Synthesis (2005), Wiley-VCH, Weinheim, Germany
24. Chen H., Wang Y., Wei S., and Sun J. Tetrahedron: Asymmetry 18 (2007) 1308
25. Tang Z., Yang Z.-H., Chen X.-H., Cun L.-F., Mi A.-Q., Jiang Y.-Z., and Gong L.-Z. J. Am. Chem. Soc. 127 (2005) 9285
26. Hayashi Y., Gotoh H., Tamura T., Yamaguchi H., Masui R., and Shoji M. J. Am. Chem. Soc. 127 (2005) 16028
27. Kano T., Yamaguchi Y., Tokuda O., and Maruoka K. J. Am. Chem. Soc. 127 (2005) 16408
28. Córdova A., Zou W., Ibrahem I., Reyes E., Engqvist M., and Liao W.-W. Chem. Commun. (2005) 3586
29. List B. Acc. Chem. Res. 37 (2004) 548
30. Notz W., Tanaka F., and Barbas III C.F. Acc. Chem. Res. 37 (2004) 580
31. Sakthivel K., Notz W., Bui T., and Barbas III C.F. J. Am. Chem. Soc. 123 (2001) 5260
32. List B., Pojarliev P.H., and Martin J. Org. Lett. 3 (2001) 2423
33. Enders D., and Seki A. Synlett (2002) 26
34. Halland N., Aburel P.S., and Jørgensen K.A. Angew. Chem., Int. Ed. 43 (2004) 1272
35. Halland N., Hansen T., and Jørgensen K.A. Angew. Chem., Int. Ed. 42 (2003) 4955
36. Halland N., Hazell R.G., and Jørgensen K.A. J. Org. Chem. 67 (2002) 8331
37. Betancort J.M., and Barbas III C.F. Org. Lett. 3 (2001) 3737
38. Betancort J.M., Sakthivel K., Thayumanavan R., and Barbas III C.F. Tetrahedron Lett. 42 (2001) 4441
39. Andrey O., Alexakis A., and Bernardinelli G. Org. Lett. 5 (2003) 2559
40. Andrey O., Vidonne A., and Alexakis A. Tetrahedron Lett. 44 (2003) 7901
41. Okino T., Hoashi Y., and Takemoto Y. J. Am. Chem. Soc. 125 (2003) 12672
42. Zhang F.-Y., and Corey E.J. Org. Lett. 2 (2000) 1097
43. Bui T., and Barbas III C.F. Tetrahedron Lett. 41 (2000) 6951
44. Mase N., Watanabe K., Yoda H., Takabe K., Tanaka F., and Barbas III C.F. J. Am. Chem. Soc. 128 (2006) 4966
45. Luo S.Z., Xu H., Mi X.L., Li J.Y., Zheng X.X., and Cheng J.-P. J. Org. Chem. 71 (2006) 9244
46. Zhong G., Fan J., and Barbas III C.F. Tetrahedron Lett. 45 (2004) 5681
47. Knudsen K.R., Mitchell C.E.T., and Ley S.V. Chem. Commun. (2006) 66
48. Bentacort J.M., Sakthivel K., Thayumanavan R., Tanaka F., and Barbas III C.F. Synthesis (2004) 1509
49. Wang J., Li H., Lou B., Zu L., Guo H., and Wang W. Chem.-Eur. J. 12 (2006) 4321