Enantioselective Michael reaction of 1,3-dicarbonyl compounds to 3-nitro-2H-chromenes catalyzed by chiral nickel complexes

Tetrahedron Letters

Volumn 51, Issue 30, 2010, Pages 3972-3974

  Chen, Wei Yi ^a   Ouyang, Luo ^b   Chen, Rui Ye ^b   Li, Xin Sheng ^b  

^a SOOCHOW UNIVERSITY   (China)

^b ZHEJIANG NORMAL UNIVERSITY   (China)

Author keywords

1,3 Dicarbonyl compound; 3 Nitro 2H chromene; Asymmetric catalysis; Chiral nickel complexes; Michael reaction

Indexed keywords

3 NITRO 2H CHROMENE DERIVATIVE; CARBONYL DERIVATIVE; CHROMENE DERIVATIVE; NICKEL COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; MICHAEL ADDITION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 77953688004     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.111     Document Type: Article

References (58)

1. Sibi M., and Manyem S. Tetrahedron 56 (2000) 8033
2. Krause N., and Hoffmann-RÖder A. Synthesis (2001) 171
3. Alexakis A., and Benhaim C. Eur. J. Org. Chem. (2002) 3221
4. Christoffers J., Koripelly G., Rosiak A., and RÖssle M. Synthesis (2007) 1279
5. Christoffers J., and Baro A. Angew. Chem., Int. Ed. 42 (2003) 1688
6. Yu Z.P., Liu X.H., Zhou L., Lin L.L., and Feng X.M. Angew. Chem., Int. Ed. 48 (2009) 5195
7. Yang X., Zhou X., Lin L.L., Chang L., Liu X.H., and Feng X.M. Angew. Chem., Int. Ed. 47 (2008) 7079
8. Mukaiyama T., and Hoshino T. J. Am. Chem. Soc. 82 (1960) 5339
9. Ono N., Miyake H., Kamimura A., Hamamoto I., Tamura R., and Kaji A. Tetrahedron 41 (1985) 4013
10. Lloyd D.H., and Nichols D.E. J. Org. Chem. 51 (1986) 4294
11. Barrett A.G.M., and Spilling C.D. Tetrahedron Lett. 29 (1988) 5733
12. Beck A.K., and Seebach D. Chem. Ber. 124 (1991) 2897
13. Maeri R.E., Heinzer J., and Seebach D. Liebigs Ann. (1995) 1193
14. Poupart M.A., Fazal G., Goulet S., and Mar L.T. J. Org. Chem. 64 (1999) 1356
15. Berner O.M., Tedeschi L., and Enders D. Eur. J. Org.Chem. (2002) 1877
16. Betancort J.M., and Barbas III C.F. Org. Lett. 3 (2001) 3737
17. Okino T., Hoashi Y., and Takemoto Y. J. Am. Chem. Soc. 125 (2003) 12672
18. Andrey O., Alexakis A., and Bernardinelli G. Org. Lett. 5 (2003) 2559
19. Enders D., and Seki A. Synlett (2002) 26
20. Cobb A.J.A., Longbottom D.A., Shaw D.M., and Ley S.V. Chem. Commun. (2004) 1808
21. Hayashi Y., Gotoh T., Hayasji T., and Shoji M. Angew. Chem., Int. Ed. 44 (2005) 4212
22. Ishii T., Fiujioka S., Sekiguchi Y., and Kotsuki H. J. Am. Chem. Soc. 126 (2004) 9558
23. Tsogoeva S.B., Yalalov D.A., Hateley M.J., Weckbecker C., and Huthmacher K. Eur. J. Org. Chem. (2005) 4995
24. McCooey S.H., and Connon S.J. Angew. Chem., Int. Ed. 44 (2005) 6367
25. Xu Y.-M., Zou W.-B., Sunden H., Ibrahem I., and Cordova A. Adv. Synth. Catal. 348 (2006) 418
26. Okino T., Hoashi Y., Furukawa T., Xu X., and Takemoto Y. J. Am. Chem. Soc. 127 (2005) 119
27. Lalonde M.P., Chen Y., and Jacobsen E.N. Angew. Chem., Int. Ed. 45 (2006) 6366
28. Yalalov D.A., Tsogoeva S.B., and Schmatz S. Adv. Synth. Catal. 348 (2006) 826
29. Herrera R.P., Sgarzani V., Bernardi L., and Ricci A. Angew. Chem., Int. Ed. 44 (2005) 6576
30. Liu K., Cui H.-F., Nie J., Dong K.-Y., Li X.-J., and Ma J.-A. Org. Lett. 9 (2007) 923
31. Wei S., Yalalov D.A., Tsogoeva S.B., and Schmatz S. Catal. Today 121 (2007) 151
32. Wang J., Li H., Duan W., Zu L., and Wang W. Org. Lett. 7 (2005) 4713
33. Tsogoeva S.B., and Wei S. Chem. Commun. (2006) 1451
34. Ye J., Dixon D.J., and Hynes P.S. Chem. Commun. (2005) 4481
35. Huang H., and Jacobsen E.N. J. Am. Chem. Soc. 128 (2006) 7170
36. Ji J., Barnes D.M., Zhang J., King S.A., Wittenberger S.J., and Morton H.E. J. Am. Chem. Soc. 121 (1999) 10215
37. Barnes D.M., Ji J., Fickes M.G., Fitzgerald M.A., King S.A., Morton H.E., Plagge F.A., Preskill M., Wagaw S.H., Wittenberger S.J., and Zhang J. J. Am. Chem. Soc. 124 (2002) 13097
38. Hiemstra H., and Wynberg H. J. Am. Chem. Soc. 103 (1981) 417
39. Hanessian S., and Pham V. Org. Lett. 2 (2000) 2975
40. Corey E.J., and Zhang F.-Y. Org. Lett. 2 (2000) 4257
41. Ooi T., Doda K., and Maruoka K. J. Am. Chem. Soc. 125 (2003) 9022
42. Halland N., Hazell R.G., and Jøgensen K.A. J. Org. Chem. 67 (2002) 8331
43. Wang J., Li H., Zu L.-S., and Wang W. Adv. Synth. Catal. 348 (2006) 425
44. Bakulya B., Varga S., CsTmpa A., and Ssos T. Org. Lett. 7 (2005) 1967
45. Wang J., Li H., Zu L.-S., Jiang W., Xie H.-X., Duan W.-H., and Wang W. J. Am. Chem. Soc. 128 (2006) 12652
46. Wu F., Hong R., Khan J., Liu X., and Deng L. Angew. Chem., Int. Ed. 45 (2006) 4301
47. Wu F., Li H., Hong R., and Deng L. Angew. Chem., Int. Ed. 45 (2006) 947
48. Hoashi Y., Okino T., and Takemoto Y. Angew. Chem., Int. Ed. 44 (2005) 4032
49. Taylor M.S., and Jacobsen E.N. J. Am. Chem. Soc. 125 (2003) 11204
50. Guerin D.J., and Miller S.J. J. Am. Chem. Soc. 124 (2002) 2136
51. Daniel D., and Rene R. Synthesis (1984) 348
52. Evans D.A., Mito S., and Seidel D. J. Am. Chem. Soc. 129 (2007) 11583
53. Fossy J.S., Matsubara R., Kiyogara H., and Kobayashi S. Inorg. Chem. 47 (2008) 781
54. Seung H.K., and Dae Y.K. Bull. Korean Chem. Soc. 30 (2009) 1439
55. Itoh K., and Kanemasa S. J. Am. Chem. Soc. 124 (2002) 13394
56. Evans D.A., and Seidel D. J. Am. Chem. Soc. 127 (2005) 9958
57. Zheng K., Shi J., Liu X.-H., and Feng X.-M. J. Am. Chem. Soc. 130 (2008) 15770
58. Itoh K., Hasegawa M., Tanaka J., and Kanemasa S. Org. Lett. 7 (2005) 979