Highly enantioselective hetero-Diels-Alder reaction between trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene and aldehydes catalyzed by (R)-BINOL-Ti(IV) complex

Tetrahedron

Volumn 61, Issue 24, 2005, Pages 5822-5830

  Gao, Bo ^a   Fu, Zhengyan ^a   Yu, Zhipeng ^a   Yu, Lan ^a   Huang, Yaozong ^a   Feng, Xiaoming ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; Dihydropyrone; Hetero Diels Alder reaction; Titanium (IV) complex

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 2,2' DIHYDROXY 1,1' BINAPHTHYL; ALDEHYDE DERIVATIVE; BENZALDEHYDE DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DIELS ALDER REACTION; ENANTIOSELECTIVITY; MUKAIYAMA REACTION; PRIORITY JOURNAL; REACTION ANALYSIS;

BETULACEAE;

EID: 19944378501     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.04.016     Document Type: Article

References (61)

1. H.B. Kagan Comprehensive Organic Chemistry Vol. 8 1992 Pergamon Oxford
2. R. Noyori Asymmetric catalysis in organic synthesis 1994 Wiley New York
3. E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis Vol. 1-3 1999 Springer Berlin
4. I. Ojima 2nd ed. Catalysis Asymmetric Synthesis 2000 Wiley New York
5. G.-Q. Lin, Y.-M. Li, and A.S.C. Chan Principles and Applications of Asymmetric Synthesis 2001 Wiley New York
6. K.A. Jørgensen Angew. Chem. Int. Ed. 39 2000 3558 3588 and references therein
7. K.A. Jørgensen Eur. J. Org. Chem. 2004 2093 2102 and references therein
8. Q. Fan, L.-L. Lin, J. Liu, Y.-Z. Huang, X.-M. Feng, and G.-L. Zhang Org. Lett. 6 2004 2185 2188
9. K. Juhl, and K.A. Jørgensen Angew. Chem. Int. Ed. 42 2003 1498 1501
10. Y. Huang, A.K. Unni, A.N. Thadani, and V.H. Rawal Nature 424 2003 146
11. H.-F. Du, D.-B. Zhao, and K.-L. Ding Chem. Eur. J. 10 2004 5964 5970
12. E.R. Larson, and S. Danishefsky J. Am. Chem. Soc. 104 1982 6458 6460
13. E.R. Larson, and S. Danishefsky Tetrahedron Lett. 23 1982 1975 1978
14. S.J. Danishefsky, E. Larson, D. Askin, and N. Kato J. Am. Chem. Soc. 107 1985 1246 1255
15. E.J. Corey, C.L. Cywin, and T.D. Roper Tetrahedron Lett. 33 1992 6907 6910
16. G.E. Keck, X.-Y. Li, and D. Krishnamurthy J. Org. Chem. 60 1995 5998 5999
17. S.E. Schaus, J. Brånalt, and E.N. Jacobsen J. Org. Chem. 63 1998 403 405
18. G.A. Molander, and R.M. Rzasa J. Org. Chem. 65 2000 1215 1217
19. C. Baldoli, S. Maiorana, E. Licandro, G. Zinzalla, M. Lanfranchi, and A. Tiripicchio Tetrahedron: Asymmetry 12 2001 2159 2167
20. Y. Yuan, J. Long, J. Sun, and K.-L. Ding Chem. Eur. J. 8 2002 5033 5042
21. Y. Yamashita, S. Saito, H. Ishitani, and S. Kobayashi J. Am. Chem. Soc. 125 2003 3793 3798
22. M.A. McCarrick, Y.-D. Wu, and K.N. Houk J. Am. Chem. Soc. 114 1992 1499 1500
23. M.A. McCarrick, Y.-D. Wu, and K.N. Houk J. Org. Chem. 58 1993 3330 3343
24. M. Roberson, A.S. Jepsen, and K.A. Jørgensen Tetrahedron 57 2001 907 913
25. G. Ujaque, P.S. Lee, K.N. Houk, M.F. Hentemann, and S.J. Danishefsky Chem. Eur. J. 8 2002 3423 3430
26. For example, see: (a) S. Danishefsky, E.R. Larson, and D. Askin J. Am. Chem. Soc. 104 1982 6457 6458
27. S. Danishefsky, and M. Bednarski Tetrahedron Lett. 26 1985 3411 3412
28. S.J. Danishefsky, W.H. Pearson, and B.E. Segmuller J. Am. Chem. Soc. 107 1985 1280 1285
29. S.J. Danishefsky, and M.P. DeNinno Angew. Chem., Int. Ed. Engl. 26 1987 15 23
30. L.F. Tietze, C. Schneider, and A. Montenbruck Angew. Chem., Int. Ed. Engl. 33 1994 980 982
31. Y.-J. Hu, X.-D. Huang, Z.-J. Yao, and Y.-L. Wu J. Org. Chem. 63 1998 2456 2461
32. M. Bednarski, and S. Danishefsky J. Am. Chem. Soc. 108 1986 7060 7067
33. W. Zhuang, J. Thorhauge, and K.A. Jørgensen Chem. Commun. 2000 459 460
34. H. Audrain, J. Thorhauge, R.G. Hazell, and K.A. Jørgensen J. Org. Chem. 65 2000 4487 4497
35. M. Bednarski, and S. Danishefsky J. Am. Chem. Soc. 105 1983 6968 6969
36. S.J. Danishefsky, H.G. Selnick, R.E. Zelle, and M.P. DeNinno J. Am. Chem. Soc. 110 1988 4368 4378
37. J.D. Rainier, S.P. Allwein, and J.M. Cox Org. Lett. 2 2000 231 234
38. J.M. Cox, and J.D. Rainier Org. Lett. 3 2001 2919 2922
39. D.R. Williams, and R.W. Heidebrecht Jr. J. Am. Chem. Soc. 125 2003 1843 1850
40. S. Danishefsky, and T. Kitahara J. Am. Chem. Soc. 96 1974 7807 7808
41. S. Danishefsky, C.-F. Yan, R.K. Singh, R.B. Gammill, P.M. McCurry Jr., N. Fritsch, and J. Clardy J. Am. Chem. Soc. 101 1979 7001 7008
42. Z.-Y. Fu, B. Gao, Z.-P. Yu, L. Yu, Y.-Z. Huang, X.-M. Feng, and G.-L. Zhang Synlett 2004 1772 1775
43. For examples of reviews on relative concepts in asymmetric synthesis, see: (a) C. Girard, and H.B. Kagan Angew. Chem. Int. Ed. 37 1998 2922 2959
44. J.W. Faller, A.R. Lavoie, and J. Parr Chem. Rev. 103 2003 3345 3368
45. K. Mikami, M. Terada, T. Korenaga, Y. Matsumoto, M. Ueki, and R. Angelaud Angew. Chem. Int. Ed. 39 2000 3532 3556
46. K. Mikami, and M. Yamanaka Chem. Rev. 103 2003 3369 3400
47. D.J. Berrisford, C. Bolm, and K.B. Sharpless Angew. Chem., Int. Ed. Engl. 34 1995 1059 1070
48. P.J. Walsh Acc. Chem. Res. 36 2003 739 749
49. K. Soai, T. Shibata, and I. Sato Acc. Chem. Res. 33 2000 382 390
50. J. Long, J.-Y. Hu, X.-Q. Shen, B.-M. Ji, and K.-L. Ding J. Am. Chem. Soc. 124 2002 10 11
51. B. Wang, X.-M. Feng, X. Cui, H. Liu, and Y.-Z. Jiang Chem. Commun. 2000 1605 1606
52. B. Wang, X.-M. Feng, Y.-Z. Huang, H. Liu, X. Cui, and Y.-Z. Jiang J. Org. Chem. 67 2002 2175 2182
53. Y.-Z. Huang, X.-M. Feng, B. Wang, G.-L. Zhang, and Y.-Z. Jiang Synlett 2002 2122 2124
54. A.S.C. Chan, F.-Y. Zhang, and C.-W. Yip J. Am. Chem. Soc. 119 1997 4080 4081
55. F.-Y. Zhang, C.-W. Yip, R. Cao, and A.S.C. Chan Tetrahedron: Asymmetry 8 1997 585 589
56. F.-Y. Zhang, and A.S.C. Chan Tetrahedron: Asymmetry 8 1997 3651 3655
57. +] 463.2091, found 463.2087.
58. D.L.J. Clive, and R.J. Bergstra J. Org. Chem. 56 1991 4976 4977 and references therein
59. M. Miyashita, T. Yamasaki, T. Shiratani, S. Hatakeyama, M. Miyazawa, and H. Irie Chem. Commun. 1997 1787 1788
60. H. Guo, and K.-L. Ding Tetrahedron Lett. 41 2000 10061 10064
61. X.-Q. Shen, H. Guo, and K.-L. Ding Tetrahedron: Asymmetry 11 2000 4321 4327