Asymmetric synthesis of β-aryl-β-trifluoromethyl-β- aminoarones via Mannich-type reactions of ketone enolates with chiral aryl CF 3-substituted N-tert-butanesulfinyl ketimines

Tetrahedron

Volumn 68, Issue 25, 2012, Pages 4955-4961

  Liu, Yingle ^a   Huang, Yangen ^a   Qing, Feng Ling ^a,b  

^a DONGHUA UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aminoarone; Asymmetric; Mannich addition; N tert Butanesulfinyl ketimine; Trifluoromethyl

Indexed keywords

2 METHYL N ((R) 1,1,1 TRIFLUORO 2(4 METHOXYPHENYL) 4 OXO 4 2 TOLYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((R) 1,1,1 TRIFLUORO 2(4 METHOXYPHENYL) 4 OXO 4 4 TOLYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((R) 1,1,1 TRIFLUORO 2(4 METHOXYPHENYL) 4 OXO 4 PHENYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((R) 1,1,1 TRIFLUORO 2,4 BIS (4 METHOXYPHENYL) 4 OXOBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((R) 1,1,1 TRIFLUORO 4 OXO 2 PHENYL 4 2 TOLYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((R) 1,1,1 TRIFLUORO 4 OXO 2 PHENYL 4 4 TOLYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((R) 1,1,1 TRIFLUORO 4 OXO 2,4 DIPHENYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((S) 1,1,1 TRIFLUORO 2(4 METHOXYPHENYL) 4 4 4 TOLYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((S) 1,1,1 TRIFLUORO 2(4 METHOXYPHENYL) 4 OXO 4 2 TOLYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((S) 1,1,1 TRIFLUORO 2(4 METHOXYPHENYL) 4 OXO 4 PHENYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((S) 1,1,1 TRIFLUORO 2,4 BIS (4 METHOXYPHENYL) 4 OXOBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((S) 1,1,1 TRIFLUORO 4 OXO 2 PHENYL 4 2 TOLYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((S) 1,1,1 TRIFLUORO 4 OXO 2 PHENYL 4 4 TOLYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((S) 1,1,1 TRIFLUORO 4 OXO 2,4 DIPHENYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; 2 METHYL N ((S) 1,1,1 TRIFLUORO 4(4 METHOXYPHENYL) 4 2 PHENYLBUTAN 2 YL) PROPANE 2 SULFINAMIDE; AROMATIC COMPOUND; AZIRIDINE DERIVATIVE; BETA ARYL TRIFLUOROMETHYL BETA AMINOARONE DERIVATIVE; IMINE; KETONE; KETONE ENOLATE DERIVATIVE; N ((R) 4(4 CHLOROPHENYL) 1,1,1 TRIFLUORO 2(4 METHOXYPHENYL) 4 OXOBUTAN 2 YL) 2 METHYLPROPANE 2 SULFINAMIDE; N ((R) 4(4 CHLOROPHENYL) 1,1,1 TRIFLUORO 4 OXO 2 PHENYLBUTAN 2 YL) 2 METHYLPROPANE 2 SULFINAMIDE; N ((S) 4(4 CHLOROPHENYL) 1,1,1 TRIFLUORO 2(4 METHOXYPHENYL) 4 OXOBUTAN 2 YL) 2 METHYLPROPANE 2 SULFINAMIDE; N ((S) 4(4 CHLOROPHENYL) 1,1,1 TRIFLUORO 4 OXO 2 PHENYLBUTAN 2 YL) 2 METHYLPROPANE 2 SULFINAMIDE; N TERT BUTANESULFINYL KETIMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; MANNICH REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84861526611     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.04.070     Document Type: Article

References (40)

1. M. Arend, B. Westermann, and N. Risch Angew. Chem., Int. Ed. 37 1998 1044
2. S.F. Martin Acc. Chem. Res. 35 2002 895
3. B. Das, P. Balasubramanyam, B. Veeranjaneyulu, and G.C. Reddy J. Org. Chem. 74 2009 9505
4. F.A. Davis, M. Song, H. Qiu, and J. Chai Org. Biomol. Chem. 7 2009 5067
5. F.A. Davis, N. Theddu, and P.M. Gaspari Org. Lett. 11 2009 1647
6. S. Joshi, A.D. Manikpuri, and P. Tiwary Bioorg. Med. Chem. Lett. 17 2007 645
7. M. Liu, and M.P. Sibi Tetrahedron 58 2002 7991
8. M.J. Gaunt, and J.B. Spencer Org. Lett. 3 2001 25
9. N. Srivastava, and B.K. Banik J. Org. Chem. 68 2003 2109
10. N.B. Ambhaikar, J.P. Snyder, and D.C. Liotta J. Am. Chem. Soc. 125 2003 3690
11. A.M. Rouhi Chem. Eng. News 82 2004 47
12. S.C. Stinson Chem. Eng. News 78 2000 55
13. H.-L. Geng, K.-X. Huang, T. Sun, W. Li, X.-W. Zhang, L. Zhou, W.-J. Wu, and X.-M. Zhang J. Org. Chem. 76 2011 332
14. I. Ojima, J.M. McCarthy, and J.T. Welch Biomedical Frontiers of Fluorine Chemistry 1996 American Chemical Society Washington, D. C
15. V.P. Kukhar, and V.. Soloshonok Fluorine-Containing Amino Acids: Synthesis and Properties 1994 Wiley Chichester, UK
16. T. Kitazume, K. Murata, A. Okabe, Y. Takanashi, and T. Yamazaki Tetrahedron: Asymmetry 5 1994 1029
17. F. Huguenot, and T. Brigaud J. Org. Chem. 71 2006 2159
18. S. Fustero, D. Jiminez, S. Cervera, F. Juan, M. Sanchez-Rosello, E. Esteban, and A. Simon-Fuentes Org. Lett. 7 2005 3433
19. K. Funabiki, M. Nagamori, S. Goushi, and M. Matsui Chem. Commun. 2004 1928
20. V.A. Sukach, N.M. Golovach, V.V. Pirozhenko, E.B. Rusanov, and M.V. Vovk Tetrahedron: Asymmetry 19 2008 761
21. J.A. Ellman, T.D. Owens, and T.P. Tang Acc. Chem. Res. 35 2002 984
22. J.A. Ellman Pure Appl. Chem. 75 2003 39
23. C.H. Senanayake, D. Krishnamurthy, Z.-H. Lu, Z. Han, and E. Gallon Aldrichimica Acta 38 2005 93
24. M. Daniel, and R.A. Stockman Tetrahedron 62 2006 8869
25. P. Zhou, B.-C. Chen, and F.A. Davis Tetrahedron 60 2004 8003
26. M.A. Robak, M.A. Herbage, and J.A. Ellman Chem. Rev. 110 2010 3600
27. J. Liu, and J. Hu Future Med. Chem. 5 2009 875
28. Y. Li, and J. Hu Angew. Chem., Int. Ed. 44 2005 5882
29. C. Ni, J. Liu, and J. Hu Angew. Chem., Int. Ed. 46 2007 786
30. J. Liu, and J. Hu Chem. - Eur. J. 16 2010 11443
31. H.-Q. Xiao, Y.-G. Huang, and F.-L. Qing Tetrahedron: Asymmetry 21 2010 2949
32. H.-B. Mei, Y.-W. Xiong, J.-J. Han, and Y. Pan Org. Biomol. Chem. 9 2011 1402
33. H. Wang, X. Zhao, Y. Li, and L. Lu Org. Lett. 8 2006 1379
34. N. Plobeck, and D. Powell Tetrahedron: Asymmetry 13 2002 303
35. W.-L. Jiang, C. Chen, C. Chen, D. Marinkovic, J.A. Tran, C.W. Chen, L.M. Arellano, N.S. White, and F.C. Tucci J. Org. Chem. 70 2005 8924
36. M.V. Vovk, N.M. Golovach, and V.A. Sukach J. Fluorine Chem. 131 2010 229
37. V.A. Sukach, N.M. Golovach, N.V. Melnichenko, I.F. Tsymbal, and M.V. Vovk J. Fluorine Chem. 129 2008 1180
38. A.S. Fisyuk, and M.A. Vorontsova Chem. Heterocycl. Compd. 6 1998 723
39. R.G. Micetich, R. Singh, and C.C. Shaw J. Org. Chem. 51 1986 1811
40. A. Alder, and D. Bellus J. Am. Chem. Soc. 105 1983 6712