A new mild base-catalyzed Mannich reaction of hetero-arylamines in water: Highly efficient stereoselective synthesis of β-aminoketones under microwave heating

Organic and Biomolecular Chemistry

Volumn 7, Issue 7, 2009, Pages 1410-1414

  Hao, Wen Juan ^a   Jiang, Bo ^a,b   Tu, Shu Jiang ^a   Cao, Xu Dong ^a   Wu, Shan Shan ^a   Yan, Shu ^a   Zhang, Xiao Hong ^a   Han, Zheng Guo ^a   Shi, Feng ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b SUZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ALDEHYDE; ARYL AMINES; HIGH-SPEED; INCREASED SAFETY; MANNICH REACTIONS; STEREOSELECTIVE SYNTHESIS; STERIC HINDRANCES; SYNTHETIC ROUTES;

ALDEHYDES; AMINES; ENVIRONMENTAL IMPACT; HEATING; MICROWAVE HEATING; MICROWAVES; STEREOCHEMISTRY; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

ALDEHYDE; AMINE; BENZOIN; DEOXYBENZOIN; DRUG DERIVATIVE; KETONE; MANNICH BASE; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HEATING; MICROWAVE RADIATION; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; AMINES; BENZOIN; CATALYSIS; HEATING; KETONES; MANNICH BASES; MICROWAVES; MOLECULAR STRUCTURE; STEREOISOMERISM; WATER;

EID: 67649404768     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b819763f     Document Type: Article

References (55)

1. R. A. Sheldon Green Chem. 2005 7 267
2. P. Anastas, T. Williamson, Green Chemistry, Frontiers in Benign Chemical Synthesis and Processes, University Press, London, 1998
3. G. W. Wang C. B. Miao Green Chem. 2006 8 1080
4. X. Wu M. Larhed Org. Lett. 2005 7 3327
5. X. Wu J. K. Ekegren M. Larhed Organometal. 2006 25 1434
6. Y. Ju R. S. Varma J. Org. Chem. 2006 71 135
7. D. Dallinger C. O. Kappe Chem. Rev. 2007 107 2563
8. J. P. Genet M. Savignac J. Organomet. Chem. 1999 576 305
9. K. H. Shaughnessy R. B. Devasher Curr. Org. Chem. 2005 9 585
10. N. E. Leadbeater Chem. Commun. 2005 2881
11. C.-J. Li Chem. Rev 2005 105 3095
12. C. I. Herrerias X. Yao Z. Li C.-J. Li Chem. Rev. 2007 107 2546
13. P. Lidstrom J. Tierney B. Wathey J. Westman Tetrahedron 2001 57 9225
14. A. Gellis N. Boufatah P. Vanelle Green Chem. 2006 8 483
15. R. Muller H. Goesmann H. Waldmann Angew. Chem., Int. Ed. 1999 38 184
16. H. Bohme and M. Haake, Adances in Organic Chemistry, E. C. Taylor, Ed.; John Wiley and Sons, New York, 1976, p 107
17. M. Suginome L. Uehlin M. Murakami J. Am. Chem. Soc. 2004 126 13196
18. W. Notz F. Tanaka S. -I. Watanabe N. S. Chowdari J. M. Turner R. Thayumanavan C. F. Barbas J. Org. Chem. 2003 68 9624
19. B. M. Trost L. R. Terrell J. Am. Chem. Soc. 2003 125 338
20. S. Matsunaga N. Kumagai S. Harada M. Shibasaki J. Am. Chem. Soc. 2003 125 4712
21. K. Juhl N. Gathergood K. A. Jorgensen Angew. Chem. 2001 113 3083
22. B. List J. Am. Chem. Soc. 2000 122 9336
23. B. List P. Pojarliev W. T. Biller H. J. Martin J. Am. Chem. Soc. 2002 124 827
24. A. Cordova W. Notz G. Zhong J. M. Betancort C. F. Barbas J. Am. Chem. Soc. 2002 124 1842
25. S. Kobayashi T. Hamada K. Manabe J. Am. Chem. Soc. 2002 124 5640
26. Y. Hayashi W. Tsuboi I. Ashimine T. Urushima M. Shoji K. Sakai Angew. Chem., Int. Ed. 2003 42 3677
27. A. G. Wenzel E. N. Jacobsen J. Am. Chem Soc. 2002 124 12964
28. D. Uraguchi K. Koshimoto T. Ooi J. Am. Chem. Soc. 2008 130 10878
29. N. S. Josephsohn M. L. Snapper A. H. Hoveyda J. Am. Chem. Soc. 2004 126 3734
30. S. Lou B. M. Taoka A. Ting S. E. Schaus J. Am. Chem. Soc. 2005 127 11256
31. N. S. Joshi L. R. Whitaker M. B. Francis J. Am. Chem. Soc. 2004 126 15942
32. L.-W. Xu C.-G. Xia L. Li J. Org. Chem. 2004 69 8482
33. W. Notz F. Tanaka C. F. Barbas Acc. Chem. Res. 2004 37 580
34. T. Hamada K. Manabe S. Kobayashi J. Am. Chem. Soc. 2004 126 7768
35. T.-P. Loh S.-L. Chen Org. Lett. 2002 4 3647
36. I. Ibrahem W. Zou M. Engqvist Y. Xu A. Cordova Chem. Eur. J. 2005 11 7024
37. A. Cordova Acc. Chem. Res. 2004 37 102
38. S. Matsunaga N. Kumagai S. Harada M. Shibasaki J. Am. Chem. Soc. 2003 125 4712
39. S. Kobayashi T. Hamada K. Manabe J. Am. Chem. Soc. 2002 124 5640
40. A. Curdova Chem.-Eur. J. 2004 10 1987
41. N. S. Chowdari J. T. Suri C. F. Barbas Org. Lett. 2004 6 2507
42. Y. Hayashi W. Tsuboi M. Shoji N. Suzuki J. Am. Chem. Soc. 2003 125 11208
43. N. S. Josephsohn E. L. Carswell M. L. Snapper A. H. Hoveyda Org. Lett. 2005 7 2711
44. H. Glombik, A. Enhsen, W. Kramer, and K.-H. Baringhaus, Eur. Pat. Appl. EP 869121 A1, 1998
45. K. Manabe S. Kobayashi Org. Lett. 1999 1 1965
46. N. Azizi L. Torkiyan M. R. Saidi Org. Lett. 2006 8 2079
47. C. O. Kappe Angew. Chem., Int. Ed. 2004 43 6250
48. L. Perreux A. Loupy Tetrahedron 2001 57 9199
49. A. Loupy C. R. Chim. 2004 7 103
50. C. O. Kappe Chem. Soc. Rev. 2008 37 1127
51. V. Polshettiwar R. S. Varma Chem. Soc. Rev. 2008 37 1546
52. T. P. Loh S. B. K. W. Liung K. L. Tan L. L. Wei Tetrahedron 2000 56 3227
53. C. Gennari I. Venturini G. Gislon G. Schimperma Tetrahedron Lett. 1987 28 227
54. G. Guanti E. Narisano L. Banfi Tetrahedron Lett. 1987 28 4331
55. H. Wu Y. Shen L.-Y. Fan Y. Wan P. Zhang C.-F. Chen W.-X. Wang Tetrahedron 2007 63 2404