Enantioselective Henry (nitroaldol) reaction catalyzed by axially chiral guanidines

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 14, 2009, Pages 3895-3898

  Ube, Hitoshi ^a   Terada, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Asymmetric catalysis; Guanidine; Henry reaction; Nitroaldol reaction; Organocatalysis

Indexed keywords

GUANIDINE; GUANIDINE DERIVATIVE; NITRO DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHIRAL CHROMATOGRAPHY; CHIRALITY; COMPLEX FORMATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; HENRY REACTION; HYDROGEN BOND; REACTION ANALYSIS; SYNTHESIS;

ALDEHYDES; CATALYSIS; GUANIDINE; HYDROGEN BONDING; NITRO COMPOUNDS; STEREOISOMERISM; TEMPERATURE;

EID: 67649647843     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.03.097     Document Type: Article

References (54)

1. For recent reviews, see:. Berkessel A., and Gröger H. Asymmetric Organocatalysis-From Biomimetic Concepts to Powerful Methods for Asymmetric Synthesis (2005), Wiley-VCH, Weinheim
2. In: Dalko P.I. (Ed). Enantioselective Organocatalysis: Reactions and Experimental Procedures (2007), Wiley & Sons, New York
3. Doyle A.G., and Jacobsen E.N. Chem. Rev. 107 (2007) 5713
4. For reviews, see:. Ishikawa T., and Isobe T. Chem. Eur. J. 8 (2002) 552
5. Ishikawa T., and Isobe T. J. Synth. Org. Chem. Jpn. 61 (2003) 58
6. Ishikawa T., and Kumamoto T. Synthesis (2006) 737
7. Leow D., and Tan C.-H. Chem. Asian J. 4 (2009) 476
8. For some excellent studies on enantioselective catalysis by chiral guanidine bases, see:. Iyer M.S., Gigstad K.M., Namdev N.D., and Lipton M. J. Am. Chem. Soc. 118 (1996) 4910
9. Corey E.J., and Grogan M.J. Org. Lett. 1 (1999) 157
10. Ishikawa T., Araki Y., Kumamoto T., Seki H., Fukuda K., and Isobe T. Chem. Commun. (2001) 245
11. Kita T., Georgieva A., Hashimoto Y., Nakata T., and Nagasawa K. Angew. Chem., Int. Ed. 41 (2002) 2832
12. Allingham M.T., Howard-Jones A., Murphy P.J., Thomas D.A., and Caulkett P.W.R. Tetrahedron Lett. 44 (2003) 8677
13. Sohtome Y., Hashimoto Y., and Nagasawa K. Adv. Synth. Catal. 347 (2005) 1643
14. Sohtome Y., Hashimoto Y., and Nagasawa K. Eur. J. Org. Chem. (2006) 2894
15. Shen J., Nguyen T.T., Goh Y.-P., Ye W., Fu X., Xu J., and Tan C.-H. J. Am. Chem. Soc. 128 (2006) 13692
16. Sohtome Y., Takemura N., Takeda K., Takagi R., Iguchi T., and Nagasawa K. Chem. Asian J. 2 (2007) 1150
17. Fu X., Jiang Z., and Tan C.-H. Chem. Commun. (2007) 5058
18. Ye W., Jiang Z., Zhao Y., Goh S.L.M., Leow D., Soh Y.-T., and Tan C.-H. Adv. Synth. Catal. 349 (2007) 2454
19. Kobayashi S., Yazaki R., Seki K., and Yamashita Y. Angew. Chem., Int. Ed. 47 (2008) 5613
20. Ryoda A., Yajima N., Haga T., Kumamoto T., Nakanishi W., Kawahata M., Yamaguchi K., and Ishikawa T. J. Org. Chem. 73 (2008) 133
21. Leow D., Shishi L., Chittimalla S.K., Fu X., and Tan C.-H. Angew. Chem., Int. Ed. 47 (2008) 5641
22. Jiang Z., Ye W., Yang Y., and Tan C.-H. Adv. Synth. Catal. 350 (2008) 2345
23. Terada M., Ube H., and Yaguchi Y. J. Am. Chem. Soc. 128 (2006) 1454
24. Terada M., Nakano M., and Ube H. J. Am. Chem. Soc. 128 (2006) 16044
25. Terada M., Ikehara T., and Ube H. J. Am. Chem. Soc. 129 (2007) 14112
26. Terada M., and Nakano M. Heterocycles 76 (2008) 1049
27. Nakano, M.; Terada, M. Synlett, in press.
28. Hannon C.L., and Anslyn E.V. Bioorganic Chemistry Frontiers Vol. 3 (1993), Springer, Berlin pp 193-255
29. Schmidtchen F.P., and Berger M. Chem. Rev. 97 (1997) 1609
30. Kratochvl B., Ondracek J., Krechl J., and Hasek J. Acta Crystallogr., Sect. C 43 (1987) 2182
31. Mueller G., Riede J., and Schmidtchen F.P. Angew. Chem., Int. Ed. 27 (1988) 1516
32. Echavarren A., Galan A., Lehn J.M., and De Mendoza J. J. Am. Chem. Soc. 111 (1989) 4994
33. Gleich A., Schmidtchen F.P., Mikulcik P., and Mueller G. J. Chem. Soc., Chem. Commun. (1990) 55
34. Also see:. Schmidtchen F.P., Gleich A., and Schummer A. Pure Appl. Chem. 61 (1989) 1535
35. van Haken E., Wynberg H., and van Bolhuis F. J. Chem. Soc., Chem. Commun. (1992) 629
36. Also see:. Boyle P.H., Convery M.A., Davis A.P., Hosken G.D., and Murray B.A. J. Chem. Soc., Chem. Commun. (1992) 239
37. For recent reviews on the asymmetric Henry reaction, see:. Boruwa J., Gogoi N., Saikia P.P., and Barua N.C. Tetrahedron: Asymmetry 17 (2006) 3315
38. Palomo C., Oiarbide M., and Laso A. Eur. J. Org. Chem. (2007) 2561
39. Sasai H., Suzuki T., Arai S., Arai T., and Shibasaki M. J. Am. Chem. Soc. 114 (1992) 4418
40. Trost B.M., and Yeh V.S.C. Angew. Chem., Int. Ed. 41 (2002) 861
41. Evans D.A., Seidel D., Rueping M., Lam H.W., Shaw J.T., and Downey C.W. J. Am. Chem. Soc. 125 (2003) 12692
42. Palomo C., Oiarbide M., and Laso A. Angew. Chem., Int. Ed. 44 (2005) 3881
43. Xiong Y., Wang X., Huang X., Wen Y., and Feng X. Chem. Eur. J. 13 (2007) 829
44. Ma K., and You J. Chem. Eur. J. 13 (2007) 1863
45. Bandini M., Piccinelli F., Tommasi S., Umani-Ronchi A., and Ventrici C. Chem. Commun. (2007) 616
46. Blay G., Domingo L.R., Hernandez-Olmos V., and Pedro J.R. Chem. Eur. J. 14 (2008) 4725
47. Chinchilla R., Najera C., and Sanchez-Agullo P. Tetrahedron: Asymmetry 5 (1994) 1393
48. Ooi T., Doda K., and Maruoka K. J. Am. Chem. Soc. 125 (2003) 2054
49. Li H., Wang B., and Deng L. J. Am. Chem. Soc. 128 (2006) 732
50. Marcelli T., van der Haas R.N.S., van Maarseveen J.H., and Hiemstra H. Angew. Chem., Int. Ed. 45 (2006) 929
51. Uraguchi D., Sakaki S., and Ooi T. J. Am. Chem. Soc. 129 (2007) 12392 Also see: Ref. 3e-g,i
52. During the course of the catalytic reaction, no epimerization occurred at the stereogenic center.
53. 3) δ 2.82 (1H, br s), 4.54 (1H, dd, J = 13.4, 3.2 Hz), 4.62 (1H, dd, J = 13.4, 9.2 Hz), 5.48 (1H, dd, J = 9.2, 3.2 Hz), 7.33-7.45 (5H, m).
54. Purkarthofer T., Gruber K., Gruber-Khadjawi M., Waich K., Skranc W., Mink D., and Griengl H. Angew. Chem., Int. Ed. 45 (2006) 3454