One-pot synthesis of chiral bicyclo[3.3.0]octatrienes using diphenylprolinol silyl ether-mediated ene-type reaction

Tetrahedron

Volumn 66, Issue 26, 2010, Pages 4894-4899

  Gotoh, Hiroaki ^a   Ogino, Hiroshi ^a   Ishikawa, Hayato ^a   Hayashi, Yujiro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Asymmetric reaction; ene Reaction; One pot reaction; Organocatalyst

Indexed keywords

ALDEHYDE DERIVATIVE; BICYCLO COMPOUND; BIPHENYL DERIVATIVE; CYCLOALKENE; CYCLOPENTADIENE DERIVATIVE; ETHER DERIVATIVE; PROLINE DERIVATIVE; SILANE DERIVATIVE;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; ENANTIOSELECTIVITY; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 77954244524     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.010     Document Type: Article

References (43)

1. H. Ishikawa, T. Suzuki, and Y. Hayashi Angew. Chem., Int. Ed. 48 2009 1304
2. Review, see V. Singh, and B. Thomas Tetrahedron 54 1998 3647
3. Y. Hayashi, H. Gotoh, T. Hayashi, and M. Shoji Angew. Chem., Int. Ed. 44 2005 4212
4. H. Gotoh, R. Masui, H. Ogino, M. Shoji, and Y. Hayashi Angew. Chem., Int. Ed. 45 2006 6853
5. H. Gotoh, and Y. Hayashi Org. Lett. 9 2007 2859
6. Y. Hayashi, T. Okano, S. Aratake, and D. Hazelard Angew. Chem., Int. Ed. 46 2007 4922
7. H. Gotoh, H. Ishikawa, and Y. Hayashi Org. Lett. 9 2007 5307
8. Y. Hayashi, H. Gotoh, R. Masui, and H. Ishikawa Angew. Chem., Int. Ed. 47 2008 4012
9. Y. Hayashi, T. Itoh, M. Ohkubo, and H. Ishikawa Angew. Chem., Int. Ed. 47 2008 4722
10. Y. Hayashi, S. Samanta, H. Gotoh, and H. Ishikawa Angew. Chem., Int. Ed. 47 2008 6634
11. Y. Hayashi, T. Okano, T. Ioth, T. Urushima, H. Ishikawa, and T. Uchimaru Angew. Chem., Int. Ed. 47 2008 9053
12. Y. Hayashi, M. Toyoshima, H. Gotoh, and H. Ishikawa Org. Lett. 11 2009 45
13. Y. Hayashi, K. Obi, Y. Ohta, D. Okamura, and H. Ishikawa Chem. Asian J. 4 2009 246
14. H. Gotoh, and Y. Hayashi Chem. Commun. 2009 3083
15. T. Itoh, H. Ishikawa, and Y. Hayashi Org. Lett. 11 2009 3854
16. H. Gotoh, D. Okamura, H. Ishikawa, and Y. Hayashi Org. Lett. 11 2009 4056
17. M. Marigo, T.C. Wabnitz, D. Fielenbach, and K.A. Jørgensen Angew. Chem., Int. Ed. 44 2005 794
18. M. Marigo, D. Fielenbach, A. Braunton, A. Kjasgaard, and K.A. Jørgensen Angew. Chem., Int. Ed. 44 2005 3703 Recent reports, see:
19. M. Nielsen, J.C. Borch, M.W. Paixao, N. Holub, and K.A. Jørgensen J. Am. Chem. Soc. 131 2009 10581
20. Reviews of diarylprolinol silyl ether, see:
21. C. Palomo, and A. Mielgo Angew. Chem., Int. Ed. 45 2006 7876
22. A. Mielgo, and C. Palomo Chem. Asian J. 3 2008 922
23. Selected reviews on organocatalysis, see:
24. P.I. Dalko, and L. Moisan Angew. Chem., Int. Ed. 43 2004 5138
25. A. Berkessel, H. Groger, Asymmetric Organocatalysis 2005 Wiley-VCH Weinheim
26. Y. Hayashi J. Synth. Org. Chem., Jpn. 63 2005 464
27. B. List Chem. Commun. 2006 819
28. M. Marigo, and K.A. Jørgensen Chem. Commun. 2006 2001
29. M.J. Gaunt, C.C.C. Johansson, A. McNally, and N.T. Vo Drug Discovery Today 12 2007 8
30. P.I. Dalko, Enantioselective Organocatalysis 2007 Wiley-VCH Weinheim
31. S. Mukherjee, J.W. Yang, S. Hoffmann, and B. List Chem. Rev. 107 2007 5471
32. C.F. Barbas III Angew. Chem., Int. Ed. 47 2008 42
33. A. Dondoni, and A. Massi Angew. Chem., Int. Ed. 47 2008 4638
34. P. Melchiorre, M. Marigo, A. Carlone, and G. Bartoli Angew. Chem., Int. Ed. 47 2008 6138
35. S. Bertelsen, and K.A. Jørgensen Chem. Soc. Rev. 38 2009 2178
36. A.G. Griesbeck J. Org. Chem. 54 1989 4981
37. Combination of amine and acid was used as a catalyst in a recent Pihko's paper and in Knoevenagel condensation.
38. A. Erkkila, and P.M. Pihko Eur. J. Org. Chem. 2007 4205
39. G. Jones Org. React. 15 1967 204
40. M.M. Gugelchuk, P.C.-M. Chan, and T.J. Sprules J. Org. Chem. 59 1994 7723
41. V. Nair, and S. Kumar Tetrahedron 52 1996 4029
42. B.-C. Hong, F.-L. Chen, S.-H. Chen, J.-H. Liao, and G.-H. Lee Org. Lett. 7 2005 557 and the references cited therein
43. B.-C. Hong, Y.-J. Shr, J.-L. Wu, A.K. Gupta, and K.-J. Lin Org. Lett. 4 2002 2249