Asymmetric Henry reaction catalyzed by a copper tridentate chiral schiff-base complex

Tetrahedron Asymmetry

Volumn 19, Issue 15, 2008, Pages 1813-1819

  Lai, Guoyin ^a   Wang, Sujing ^a   Wang, Zhiyong ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; COPPER TRIDENTATE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 49049109227     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.06.036     Document Type: Article

References (69)

1. Henry L. Compt. Rend. Hebd. Seances Acad. Sci. 120 (1895) 1265-1267
2. Rosini G. In: Trost B.M., Fleming I., and Heathcock C.H. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon, New York 321-340
3. Luzzio F.A. Tetrahedron 57 (2001) 915-945
4. Ono N. The Nitro Group in Organic Synthesis (2001), Wiley-VCH, New York
5. Sasai H., Suzuki T., Arai S., Arai T., and Shibasaki M. J. Am. Chem. Soc. 114 (1992) 4418-4420
6. Sasai H., Suzuki T., Itoh N., Tanaka K., Date T., Okamura K., and Shibasaki M. J. Am. Chem. Soc. 115 (1993) 10372-10373
7. Shibasaki M., and Yoshikawa N. Chem. Rev. 102 (2002) 2187-2209
8. Handa S., Nagawa K., Sohtome Y., Matsunaga S., and Shibasaki M. Angew. Chem., Int. Ed. 47 (2008) 3230-3233
9. Nitabaru T., Kumagai N., and Shibasaki M. Tetrahedron Lett. 49 (2008) 272-276
10. Trost B.M., and Yeh V.S.C. Angew. Chem., Int. Ed. 41 (2002) 861-863
11. Trost B.M., Yeh V.S.C., Ito H., and Bremeyer N. Org. Lett. 4 (2002) 2621-2623
12. Evans D.A., Seidel D., Rueping M., Lam H.W., Shaw J.T., and Downey C.W. J. Am. Chem. Soc. 125 (2003) 12692-12693
13. Palomo C., Oiarbide M., and Mielgo A. Angew. Chem., Int. Ed. 43 (2004) 5442-5444
14. Palomo C., Oiarbide M., and Laso A. Angew. Chem., Int. Ed. 44 (2005) 3881-3884
15. Christensen C., Juhl K., and Jørgensen K.A. Chem. Commun. (2001) 2222-2223
16. Christensen C., Juhl K., Hazell R.G., and Jørgensen K.A. J. Org. Chem. 67 (2002) 4875-4881
17. For other studies on metal based catalysts see:. Klein G., Pandiaraju S., and Reiser O. Tetrahedron Lett. 43 (2002) 7503-7506
18. Ooi T., Doda K., and Maruoka K. J. Am. Chem. Soc. 125 (2003) 2054-2055
19. Kogami Y., Nakajima T., Ikeno T., and Yamada T. Synthesis (2004) 1947-1950
20. Kogami Y., Nakajima T., Ashizawa T., Kezuka S., Ikeno T., and Yamada T. Chem. Lett. 33 (2004) 614-615
21. In: Mahrwald R. (Ed). Modern Aldol Reactions (2004), Wiley-VCH, Weinheim
22. Zhong Y.-W., Tian P., and Lin G.-Q. Tetrahedron: Asymmetry 15 (2004) 771-776
23. Saá J.M., Tur F., González J., and Vega M. Tetrahedron: Asymmetry 17 (2006) 99-106
24. Misumi Y., and Matsumoto K. Angew. Chem., Int. Ed. (2002) 1031-1033
25. Arai T., Watanabe M., Fujiwara A., Yokoyama N., and Yanagisawa A. Angew. Chem., Int. Ed. 45 (2006) 5978-5981
26. Vongvilai P., Angelin M., Larsson R., and Ramström O. Angew. Chem., Int. Ed. 46 (2007) 948-950
27. Gao J., and Martell A.E. Org. Biomol. Chem. 1 (2003) 2801-2806
28. Maheswaran H., Prasanth K.L., Krishna G.G., Ravikumar K., Sridhar B., and Kantam M.L. Chem. Commun. (2006) 4066-4068
29. Bandini M., Piccinelli F., Tommasi S., Umani-Ronchi A., and Ventrici C. Chem. Commun. (2007) 616-618
30. Choudary B.M., Ranganath K.V.S., Pal U., Kantam M.L., and Sreedhar B. J. Am. Chem. Soc. 127 (2005) 13167-13171
31. Blay G., Climent E., Ferna'ndez I., Herna'ndez-Olmos V., and Pedro J.R. Tetrahedron: Asymmetry 17 (2006) 2046-2049
32. Bhatt A.P., Pathak K., Jasra R.V., Kureshy R.I., Khan N.H., and Abdi S.H.R. J. Mol. Catal. A: Chem. 244 (2006) 110-117
33. Xiong Y., Wang F., Huang X., Wen Y., and Feng X. Chem. Eur. J. 13 (2007) 829-833
34. Ma K., and You J. Chem. Eur. J. 13 (2007) 1863-1871
35. Bandini M., Benaglia M., Sinisi R., Tommasi S., and Umani-Ronchi A. Org. Lett. 9 (2007) 2151-2153
36. Arai T., Watanabe M., and Yanagisawa A. Org. Lett. 9 (2007) 3595-3597
37. Mansawat W., Saengswang I., U-prasitwong P., Bhanthumnavin W., and Vilaivan T. Tetrahedron Lett. 48 (2007) 4235-4238
38. Gruber-Khadjawi M., Purkarthofer T., Skranc W., and Griengla H. Adv. Synth. Catal. 349 (2007) 1445-1450
39. Lu S.-F., Du D.-M., Zhang S.-W., and Xu J. Tetrahedron: Asymmetry 15 (2004) 3433-3441
40. Du D.-M., Lu S.-F., Fang T., and Xu J. J. Org. Chem. 70 (2005) 3712-3715
41. Vongvilai P., Larsson R., and Ramström O. Adv. Synth. Catal. 350 (2008) 448-452
42. Liu X., Jiang J., and Shi M. Tetrahedron: Asymmetry 18 (2007) 2773-2781
43. Çolak M., and Demirel N. Tetrahedron: Asymmetry 19 (2008) 635-639
44. Qin B., Xiao X., Liu X., Huang J., Wen Y., and Feng X. J. Org. Chem. 72 (2007) 9323-9328
45. For organocatalysts see:. Sohtome Y., Hashimoto Y., and Nagasawa K. Adv. Synth. Catal. 347 (2005) 1643-1648
46. Sohtome Y., Hashimoto Y., and Nagasawa K. Eur. J. Org. Chem. (2006) 2894-2897
47. Marcelli T., van der Haas R.N.S., van Maarseveen J.H., and Hiemstra H. Angew. Chem., Int. Ed. 45 (2006) 929-931
48. Marcelli T., van der Haas R.N.S., van Maarseveen J.H., and Hiemstra H. Angew. Chem., Int. Ed. 45 (2006) 7496-7504
49. Taylor M.S., and Jacobsen E.N. Angew. Chem. Int. Ed. 45 (2006) 1520-1543
50. Connon S.J. Chem. Eur. J. 12 (2006) 5418-5427
51. Pihko P.M. Angew. Chem., Int. Ed. 43 (2004) 2062-2064
52. Schreiner P.R. Chem. Soc. Rev. 32 (2003) 289-296
53. Li H., Wang B., and Deng L. J. Am. Chem. Soc. 128 (2006) 732-733
54. Takada K., Takemura N., Cho K., Sohtome Y., and Nagasawa K. Tetrahedron Lett. 49 (2008) 1623-1626
55. For the reviews on the asymmetric Henry reaction see:. Palomo C., Oiarbide M., and Laso A. Eur. J. Org. Chem. (2007) 2561-2574
56. Boruwa J., Gogoi N., Saikia P.P., and Barua N.C. Tetrahedron: Asymmetry 17 (2006) 3315-3326
57. For views on the use of Schiff-base in organic synthesis see:. Li Z.-N., Zheng Z., and Chen H. Tetrahedron: Asymmetry 11 (2000) 1157-1163
58. Cai L., Mahmoud H., and Han Y. Tetrahedron: Asymmetry 10 (1999) 411-427
59. Aratani T., Yoneyoshi Y., and Nagase T. Tetrahedron Lett. 23 (1982) 685-688
60. Aratani T. Pure Appl. Chem. 57 (1985) 1839-1844
61. Itagaki M., Hagiya K., Kamitamari M., Masumoto K., Suenobu K., and Yamamoto Y. Tetrahedron 60 (2004) 7835-7843
62. Jarvo E.R., Lawrence B.M., and Jacobsen E.N. Angew. Chem., Int. Ed. 44 (2005) 6043-6046
63. Gademann K., Chavez D.E., and Jacobsen E.N. Angew. Chem., Int. Ed. 41 (2002) 3059-3061
64. Dossetter A.G., Jamison T.F., and Jacobsen E.N. Angew. Chem., Int. Ed. 38 (1999) 2398-2400
65. Ruck R.T., and Jacobsen E.N. Angew. Chem., Int. Ed. 42 (2003) 4771-4774
66. Ruck R.T., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 2882-2883
67. Gama A., Flores-López L.Z., Aguirre G., Parra-Hake M., Somanathan R., and Cole T. Tetrahedron: Asymmetry 16 (2005) 1167-1174
68. Gan C., Lai G., Zhang Z., Wang Z., and Zhou M.-M. Tetrahedron: Asymmetry 17 (2006) 725-728
69. 2. Crystallographic data for the structure reported in this Letter have been deposited with the Cambridge Crystallographic Data Centre and allocated the deposition numbers: CCDC 672046. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EW, UK (Fax: Int code+(1223) 336-033; E-mail: deposit@ccdc.cam.ac.uk).