Enantioselective Michael addition of 3(2H)-furanones to α,β-unsaturated aldehydes catalyzed by a diphenylprolinol silyl ether

Tetrahedron Letters

Volumn 55, Issue 1, 2014, Pages 209-211

  He, Wujun ^a   Jing, Linhai ^a   Qin, Dabin ^a   Xie, Xiaohua ^a   Wu, Song ^a   Wang, Rongming ^a  

^a CHINA WEST NORMAL UNIVERSITY   (China)

Author keywords

, Unsaturated aldehyde; 3(2H) Furanone; Asymmetric catalysis; Michael addition; Quaternary carbon center

Indexed keywords

2,3 UNSATURATED ALDEHYDE; 3(2H) FURANONE; ALDEHYDE; DIPHENYLPROLINOL SILYL ETHER; EREMANTHOLIDE; ETHER; FURANONE DERIVATIVE; HETEROCYCLIC COMPOUND; HYPEROLACTONE A; HYPEROLACTONE B; HYPEROLACTONE C; JATROPHONE; LACTONE DERIVATIVE; NATURAL PRODUCT; OXYGEN; PSEUROTIN; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 84890165518     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.10.150     Document Type: Article

References (57)

1. For selected reviews, see: M.C. Elliott J. Chem. Soc., Perkin Trans. 1 2000 1291 1318
2. M.C. Elliott, and E. Williams J. Chem. Soc., Perkin Trans. 1 2001 2303 2340
3. M.C. Elliott J. Chem. Soc., Perkin Trans. 1 2002 2301 2323
4. A. Deiters, and S.F. Martin Chem. Rev. 104 2004 2199 2238
5. S. Schroter, C. Stock, and T. Bach Tetrahedron 61 2005 2245 2267
6. I.J.S. Fairlamb Chem. Soc. Rev. 36 2007 1036 1045
7. R.H. Bates, M. Chen, and W.R. Roush Curr. Opin. Drug Discov. Dev. 11 2008 778 792
8. A.M. Helguera, G. Perez-Machado, M. Cordeiro, and F. Borges Mini-Rev. Med. Chem. 12 2012 907 919
9. S.M. Kupchan, C.W. Sigel, M.J. Matz, J.A.S. Renauld, R.C. Haltiwanger, and R.F. Bryan J. Am. Chem. Soc. 92 1970 4476 4477
10. S.M. Kupchan, C.W. Sigel, M.J. Matz, C.J. Gilmore, and R.F. Bryan J. Am. Chem. Soc. 98 1976 2295 2300
11. M.D. Taylor, A.B. Smith, G.T. Furst, S.P. Gunasekara, C.A. Bevelle, G.A. Cordell, N.R. Farnsworth, S.M. Kupchan, H. Uchida, A.R. Branfman, R.G. Dailey, and A.T. Sneden J. Am. Chem. Soc. 105 1983 3177 3183
12. J.B. Calixto, and A.E.G. Santana Gen. Pharmacol. 21 1990 117 122
13. V.L.G. de Moraes, V.M. Rumjanek, and J.B. Calixto Eur. J. Pharmacol. 312 1996 333 339
14. F.V. Dutra, J.B. Calixto, Y.S. Medeiros, and R. Brum Phytother. Res. 10 1996 271 273
15. G. SchmedaHirschmann, I. Razmilic, M. Sauvain, C. Moretti, V. Munoz, E. Ruiz, E. Balanza, and A. Fournet Phytother. Res. 10 1996 375 378
16. A.F. dos Santos, and A.E.G. Sant'Ana Phytother. Res. 13 1999 660 664
17. W. Zhang, and Y.W. Guo Planta Med. 71 2005 283 286
18. C. Theoduloz, J.A. Rodriguez, M. Pertino, and G. Schmeda-Hirschmann Planta Med. 75 2009 1520 1522
19. R.F. Raffauf, P.K.C. Huang, P.W. Lequesne, S.B. Levery, and T.F. Brennan J. Am. Chem. Soc. 97 1975 6884 6886
20. P.W. Le Quesne, S.B. Levery, M.D. Menachery, T.F. Brennan, and R.F. Raffauf J. Chem. Soc., Perkin Trans. 1 1978 1572 1580
21. P. Bloch, C. Tamm, P. Bollinger, T.J. Petcher, and H.P. Weber Helv. Chim. Acta 59 1976 133 137
22. W. Breitenstein, K.K. Chexal, P. Mohr, and C. Tamm Helv. Chim. Acta 64 1981 379 388
23. J. Wenke, H. Anke, and O. Sterner Biosci. Biotechnol. Biochem. 57 1993 961 964
24. D. Komagata, S. Fujita, N. Yamashita, S. Saito, and T. Morino J. Antibiot. 49 1996 958 959
25. S. Maiya, A. Grundmann, X. Li, S.M. Li, and G. Turner ChemBioChem 8 2007 1736 1743
26. M. Ishikawa, T. Ninomiya, H. Akabane, N. Kushida, G. Tsujiuchi, M. Ohyama, S. Gomi, K. Shito, and T. Murata Bioorg. Med. Chem. Lett. 19 2009 1457 1460
27. M.A.U. Mehedi, A.H. Molla, P. Khondkar, S. Sultana, M.A. Islam, M.A. Rashid, and R. Chowdhury Asian J. Chem. 22 2010 2611 2614
28. F.Z. Wang, D.H. Li, T.J. Zhu, M. Zhang, and Q.Q. Gu Can. J. Chem. Rev. Can. Chim. 89 2011 72 76
29. M. Tada, M. Nagai, C. Okumura, Y. Osano, and T. Matsuzaki Chem. Lett. 1989 683 686
30. Y. Aramaki, K. Chiba, and M. Tada Phytochemistry 38 1995 1419 1421
31. C.M. Marson, E. Edaan, J.M. Morrell, S.J. Coles, M.B. Hursthouse, and D.T. Davies Chem. Commun. 2007 2494 2496
32. For the examples of enantioselective synthesis of jatrophone, see: A.B. Smith, M.A. Guaciaro, S.R. Schow, P.M. Wovkulich, B.H. Toder, and T.W. Hall J. Am. Chem. Soc. 103 1981 219 222
33. Q. Han, and D.F. Wiemer J. Am. Chem. Soc. 114 1992 7692 7697
34. For the examples of enantioselective synthesis of eremantholide, see: R.K. Boeckman, S.K. Yoon, and D.K. Heckendorn J. Am. Chem. Soc. 113 1991 9682 9684
35. K. Takao, H. Ochiai, T. Hashizuka, H. Koshimura, K. Tadano, and S. Ogawa Tetrahedron Lett. 36 1995 1487 1490
36. K. Takao, H. Ochiai, K. Yoshida, T. Hashizuka, H. Koshimura, K. Tadano, and S. Ogawa J. Org. Chem. 60 1995 8179 8193
37. K. Takao, J. Ishihara, and K. Tadano J. Synth. Org. Chem Jpn. 56 1998 1026 1035
38. Y. Li, and K.J. Hale Org. Lett. 9 2007 1267 1270
39. D.C. Sass, V.C. Gomes Heleno, J.L. Callegari Lopes, and M.G. Constantino Tetrahedron Lett. 49 2008 3877 3880
40. For the examples of enantioselective synthesis of pseurotin, see: P. Mohr, and C. Tamm Tetrahedron 37 1981 201 212
41. Y. Hayashi, M. Shoji, S. Yamaguchi, T. Mukaiyama, J. Yamaguchi, H. Kakeya, and H. Osada Org. Lett. 5 2003 2287 2290
42. For the examples of enantioselective synthesis of hyperolactone, see: T. Ueki, D. Ichinari, K. Yoshihara, Y. Morimoto, and T. Kinoshita Tetrahedron Lett. 39 1998 667 668
43. D.M. Hodgson, D. Angrish, S.P. Erickson, J. Kloesges, and C.H. Lee Org. Lett. 10 2008 5553 5556
44. C. Du, L.Q. Li, Y. Li, and Z.X. Xie Angew. Chem., Int. Ed. 48 2009 7853 7856
45. D.M. Hodgson, and S. Man Chem. Eur. J. 17 2011 9731 9737
46. For reviews on applications of the diarylprolinol silyl ether catalysts, see: C. Palomo, and A. Mielgo Angew. Chem., Int. Ed. 45 2006 7876 7880
47. P. Melchiorre, M. Marigo, A. Carlone, and G. Bartoli Angew. Chem., Int. Ed. 47 2008 6138 6171
48. A. Mielgo, and C. Palomo Chem. Asian J. 3 2008 922 948
49. S. Bertelsen, and K.A. Jørgensen Chem. Soc. Rev. 38 2009 2178 2189
50. L.-W. Xu, L. Li, and Z.-H. Shi Adv. Synth. Catal. 352 2010 243 279
51. L. Albrecht, L.K. Ransborg, and K.A. Jørgensen Catal. Sci. Technol. 2 2012 1089 1098
52. K.L. Jensen, G. Dickmeiss, H. Jiang, Ł. Albrecht, and K.A. Jørgensen Acc. Chem. Res. 45 2012 248 264
53. For seminal examples using diarylprolinol silyl ether catalysts, see: M. Marigo, T.C. Wabnitz, D. Fielenbach, and K.A. Jørgensen Angew. Chem., Int. Ed. 44 2005 794 797
54. M. Marigo, D. Fielenbach, A. Braunton, A. Kjærsgaard, and K.A. Jørgensen Angew. Chem., Int. Ed. 44 2005 3703 3706
55. Y. Hayashi, H. Gotoh, T. Hayashi, and M. Shoji Angew. Chem., Int. Ed. 44 2005 4212 4215
56. M. Marigo, J. Franzén, T.B. Poulsen, W. Zhuang, and K.A. Jørgensen J. Am. Chem. Soc. 127 2005 6964 6965
57. CCDC-953551 (5l) contains the supplementary crystallographic data for this Letter. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.