Organocatalytic asymmetric one-pot sequential reaction: Synthesis of highly substituted spirocyclohexanepyrazolones with six contiguous stereogenic carbons

Tetrahedron

Volumn 70, Issue 49, 2014, Pages 9330-9336

  Sun, Ping ^a   Meng, Chang Yu ^b   Zhou, Feng ^a   Li, Xin Sheng ^a   Xie, Jian Wu ^a  

^a ZHEJIANG NORMAL UNIVERSITY   (China)

^b YULIN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DICARBONYL COMPOUND; 3 CYANO 2 IMINO 3',8 A DIMETHYL 5' OXO 1',5,7 TRIPHENYL 1',2,4 A,5,5',7,8,8 A OCTAHYDROSPIRO[CHROMENE 6,4' PYRAZOLE] 8 CARBOXYLATE; ALDEHYDE DERIVATIVE; ALPHA BETA UNSATURATED ALDEHYDE; CARBONYL DERIVATIVE; CYCLOHEXANE DERIVATIVE; ETHYL 10 (2 CHLOROPHENYL) 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6 DIPHENYL 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 10 (3 BROMOPHENYL) 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6 DIPHENYL 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 10 (3 CHLOROPHENYL) 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6 DIPHENYL 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 10 (4 BROMOPHENYL) 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6 DIPHENYL 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATEYIELD; ETHYL 10 (4 CHLOROPHENYL) 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6 DIPHENYL 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 10 (4 FLUOROPHENYL) 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6 DIPHENYL 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 6 (3 BROMOPHENYL) 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,10 DIPHENYL 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 9 (2,2 DICYANOVINYL) 8 HYDROXYL 1,8 DIMETHYL 4 OXO 3,6,10 TRIPHENYL 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 9 FORMYL 1,8 DIMETHYL 4 OXO 3,6,10 TRIPHENYL 2,3 DIAZASPIRO[4.5]DECA 1,8 DIENE 7 CARBOXYLATE; ETHYL 9 FORMYL 10 (FURAN 3 YL) 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6 DIPHENYL 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 10 (4 NITROPHENYL) 4 OXO 3,6 DIPHENYL 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6 DIPHENYL 10 (M TOLYL) 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6 DIPHENYL 10 (O TOLYL) 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6 DIPHENYL 10 (P METHOXYPHENY) 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6 DIPHENYL 10 (P TOLYL) 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; ETHYL 9 FORMYL 8 HYDROXY 1,8 DIMETHYL 4 OXO 3,6,10 TRIPHEN; ETHYL 9 FORMYL 8 HYDROXY 1,8,10 TRIMETHYL 4 OXO 3,6 DIPHENYL 2,3 DIAZASPIRO[4.5]DEC 1 ENE 7 CARBOXYLATE; POLYFUNCTIONAL GROUP; PYRAZOLONE DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE; ONE POT SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 84921847897     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.10.038     Document Type: Article

References (39)

1. K.C. Nicolaou, D.J. Edmonds, and P.G. Bulger Angew. Chem. 118 2006 7292
2. Angew. Chem., Int. Ed. 45 2006 7134
3. C.J. Chapman, and C.G. Frost Synthesis 1 2007
4. C. Grondal, M. Jeanty, and D. Enders Nat. Chem. 2 2010 167
5. For an excellent book about the chemistry of pyrazol-3-ones: G. Varvounis A.R. Katritzky, Pyrazol-3-ones. Part IV: Synthesis and Applications Adv. Heterocyclic Chem. Vol. 98 2009 Academic 143 223
6. Y. Li, S. Zhang, J. Yang, S. Jiang, and Q. Li Dyes Pigm. 76 2008 508
7. K. Sujatha, G. Shanthi, N.P. Selvam, S. Manoharan, P.T. Perumal, and M. Rajendran Bioorg. Med. Chem. Lett. 19 2009 4501
8. D. Costa, A.P. Marques, R.L. Reis, J.L.F.C. Lima, and E. Fernandes Free Radic. Biol. Med. 40 2006 632
9. S. Bondock, R. Rabie, H.A. Etman, and A.A. Fadda Eur. J. Med. Chem. 43 2008 2122
10. R.N. Brogden Drugs 32 1986 60
11. C. Pégurier, P. Collart, P. Danhaive, S. Defays, M. Gillard, F. Gilson, T. Kogej, P. Pasau, N. Van Houtvin, M. Van Thuyne, and B. Van Keulen Bioorg. Med. Chem. Lett. 17 2007 4228
12. J.S. Casas, E.E. Castellano, Ellena, M.S. Garcia-Tasende, M.L. Peres-Paralle, A. Sanchez, A. Sanchez-Gonzalez, J. Sordo, and A. Touceda J. Inorg. Biochem. 102 2008 33
13. T.W. Wu, L.H. Zeng, J. Wu, and K.P. Fung Life Sci. 71 2002 2249
14. Y.-H. Liao, W.-B. Chen, Z.-J. Wu, X.-L. Du, L.-F. Cun, X.-M. Zhang, and W.-C. Yuan Adv. Synth. Catal. 352 2010 827
15. L.-P. Liu, Y. Zhong, P.-P. Zhang, X.-X. Jiang, and R. Wang J. Org. Chem. 77 2012 10228
16. A. Mazzanti, T. Calbet, M. Font-Bardia, A. Moyano, and R. Rios Org. Biomol. Chem. 10 2012 1645
17. X. Companyó, A. Zea, A. Nekane, R. Alba, A. Mazzanti, A. Moyano, and R. Rios Chem. Commun. 2010 6953
18. A. Zea, A. Nekane, R. Alba, A. Mazzanti, A. Moyano, and R. Rios Org. Biomol. Chem. 9 2011 6519
19. J.-X. Zhang, N.-K. Li, Z.-M. Liu, X.-F. Huang, Z.-C. Geng, and X.-W. Wang Adv. Synth. Catal. 355 2013 797
20. J.-Y. Liang, Q. Chen, L.-P. Liu, X.-X. Jiang, and R. Wang Org. Biomol. Chem. 11 2013 1441
21. A.N.R. Alba, A. Zea, G. Valero, T. Calbet, M. Font-Bardía, A. Mazzanti, A. Moyano, and R. Rios Eur. J. Org. Chem. 7 2011 1318
22. B. Wu, J. Chen, M.-Q. Li, J.-X. Zhang, X.-P. Xu, S.-J. Ji, and X.-W. Wang Eur. J. Org. Chem. 7 2012 1318
23. P. Chauhan, S. Mahajan, C.C.J. Loh, G. Raabe, and D. Enders Org. Lett. 16 2014 2954
24. Z.-L. Tao, W.-Q. Zhang, D.-F. Chen, A. Adele, and L.-Z. Gong J. Am. Chem. Soc. 135 2013 9255
25. J.-T. Li, X.-J. Lian, X.-H. Liu, L.-L. Lin, and X.-M. Feng Chem. - Eur. J. 19 2013 5134
26. Z.-G. Yang, Z. Wang, S. Bai, X.-H. Liu, L.-L. Lin, and X.-M. Feng Org. Lett. 13 2011 596
27. B.-D. Cui, S.-W. Li, J. Zuo, Z.-J. Wu, X.-M. Zhang, and W.-C. Yuan Tetrahedron 2014 1895
28. H.-M. Zhang, H. Lv, and S. Ye Org. Biomol. Chem. 11 2013 6255
29. Q. Chen, J. Liang, S. Wang, D. Wang, and R. Wang Chem. Commun. 2013 1657
30. J.C. Wasilke, S.J. Obrey, R.T. Baker, and G.C. Bazan Chem. Rev. 105 2005 1001
31. L.F. Tietze Chem. Rev. 96 1996 115
32. D. Enders, G. Urbanietz, E. Cassens-Sasse, S. Keeß, and G. Raabe Adv. Synth. Catal. 354 2012 1481
33. J.-W. Xie, M.-L. Xu, R.-Z. Zhang, J.-Y. Pan, and W.-D. Zhu Adv. Synth. Catal. 356 2014 395
34. Z.-W. Guo, J.-W. Xie, C. Chen, and W.-D. Zhu Org. Biomol. Chem. 10 2012 847
35. L.-P. Fan, P. Li, X.-S. Li, D.-C. Xu, M.-M. Ge, W.-D. Zhu, and J.-W. Xie J. Org. Chem. 75 2010 8716
36. T. Okino, Y. Hoashi, and Y. Takemoto J. Am. Chem. Soc. 125 2003 12672
37. T. Okino, Y. Hoashi, T. Furukawa, X. Xu, and Y. Takemoto J. Am. Chem. Soc. 127 2005 119 For cinchona-derived bifunctional thioureas, see
38. S. Tian, Y. Chen, J. Hang, L. Tang, P. McDaid, and L. Deng Acc. Chem. Res. 2004 For pyrrolidine-thiourea see
39. C.-L. Cao, M.-C. Ye, X.-L. Sun, and Y. Tang Org. Lett. 8 2006 2901