Bifunctional phosphine-catalyzed domino reaction: Highly stereoselective synthesis of cis-2,3-dihydrobenzofurans from salicyl N-thiophosphinyl imines and allenes

Organic Letters

Volumn 11, Issue 1, 2009, Pages 137-140

  Meng, Xiangtai ^a   Huang, You ^a   Chen, Ruyu ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

(2' HYDROXYBIPHENYL 2 YL)DIETHYLPHOSPHANE; (2'-HYDROXYBIPHENYL-2-YL)DIETHYLPHOSPHANE; ALKADIENE; BENZOFURAN DERIVATIVE; BIPHENYL DERIVATIVE; COUMARAN; IMINE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKADIENES; BENZOFURANS; BIPHENYL COMPOUNDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; IMINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHINES; STEREOISOMERISM;

EID: 59649089547     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802453c     Document Type: Article

References (88)

1. For reviews on domino reactions, see: (a) Tietze, L. F.; Brasche, G.; Gericke, K.; Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006.
2. (b) Guo, H.-C.; Ma, J.-A. Angew. Chem. Int. Ed. 2006, 45, 354.
3. (c) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. 1993, 32, 131.
4. (d) Tietze, L. F. Chem. Rev. 1996, 96, 115.
5. For recent reviews on organocatalytic domino reactions, see: Enders, D.; Grondal, C.; Huttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
6. For recent examples on domino reactions catalyzed by prolinol derivatives see: (a) Penon, O.; Carlone, A.; Mazzanti, A.; Locatelli, M.; Sambri, L.; Bartoli, G.; Melchiorre, P. Chem.-Eur. J. 2008, 14, 4788.
7. (b) Zhu, M. K.; Wei, Q.; Gong, L. Z. Adv. Synth. Catal. 2008, 350, 1281.
8. (c) Zhao, G. L.; Vesely, J.; Rios, R.; Ibrahem, I.; Sundén, H.; Córdova, A. Adv. Synth. Catal. 2008, 350, 237.
9. (d) Enders, D.; Hüttl, M. R. M.; Raabe, G.; Bats, J. W. Adv. Synth. Catal. 2008, 350, 267.
10. (e) Cabrera, S.; Alemán, J.; Bolze, P.; Bertelsen, S.; Jøgensen, K. A. Angew. Chem., Int. Ed. 2008, 47, 121.
11. (f) Franke, P. T.; Johansen, R. L.; Bertelsen, S.; Jøogensen, C K. A. Chem. Asian J. 2008, 3, 216.
12. (g) Franke, P. T.; Richter, B.; Jøgensen, K. A. Chem. Eur. J. 2008, 14, 6317.
13. (h) Zu, L.; Xie, H.; Li, H.; Wang, J.; Yu, X.; Wang, W. Chem.-Eur. J. 2008, 14, 6333.
14. (i) Carlone, A.; Cabrera, S.; Marigo, M.; Jøgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1101.
15. (j) Sundén, H.; Ibrahem, I.; Zhao, G.-L.; Eriksson, L.; Córdova, A. Chem.-Eur. J. 2007, 13, 574.
16. (k) Hayashi, Y.; Okano, T.; Aratake, S.; Hazelard, D. Angew. Chem., Int. Ed. 2007, 46, 4922.
17. (l) Vicario, J. L.; Reboredo, S.; Badía, D.; Carrillo, L. Angew. Chem., Int. Ed. 2007, 46, 5168.
18. (m) Reyes, E.; Jiang, H.; Milelli, A.; Elsner, P.; Hazell, R. G.; Jøgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 9202.
19. (n) Xie, H.-X.; Zu, L.-S.; Li, H.; Wang, J.; Wang, W. J. Am. Chem. Soc. 2007, 129, 10886.
20. (o) Li, H.; Zu, L.-S.; Xie, H.-X.; Wang, J.; Jiang, W.; Wang, W. Org. Lett. 2007, 9, 1833.
21. (p) Wang, J.; Li, H.; Xie, H.-X.; Zu, L.-S.; Shen, X.; Wang, W. Angew. Chem. Int. Ed. 2007, 46, 9050.
22. (q) Zu, L.-S.; Li, H.; Xie, H.-X.; Wang, J.; Jiang, W.; Tang, Y.; Wang, W. Angew. Chem., Int. Ed. 2007, 46, 3732.
23. (r) Wang, W.; Li, H.; Wang, J.; Zu, L.-S. J. Am. Chem. Soc. 2006, 128, 10354.
24. (s) Brandau, S.; Maerten, E.; Jøgensen, K. A. J. Am. Chem. Soc. 2006, 128, 14986.
25. (t) Enders, D.; Hüttl, M. R. M.; Grondal, C. Nature 2006, 441, 861.
26. (u) Marigo, M.; Schulte, T.; Franzén, J.; Jøgensen, K. A. J. Am. Chem. Soc. 2005, 127, 15710.
27. For selected examples of Cinchona Alkaloid, amine thiourea catalyzed domino reactions, see: (a) Wang, J.; Xie, H.; Li, H.; Zu, L.; Wang, W. Angew. Chem., Int. Ed. 2008, 47, 4177.
28. (b) Dodda, R.; Goldman, J. J.; Mandal, T.; Zhao, C.-G.; Broker, G. A.; Tiekink, E. R. T. Adv. Synth. Catal. 2008, 350, 537.
29. (c) Zu, L.-S.; Xie, H.-X.; Li, H.; Wang, J.; Jiang, W.; Wang, W. Ady. Synth. Catal. 2007, 349, 1882.
30. (d) Wang, B.; Wu, F.; Wang, Y.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2007, 129, 768.
31. (e) Zu, L.-S.; Wang, J.; Li, H.; Xie, H.-X.; Jiang, W.; Wang, W. J. Am. Chem. Soc. 2007, 129, 1036.
32. (f) Biddle, M. M.; Lin, M.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 3830.
33. (g) Wang, Y.; Liu, X.-F.; Deng, L. J. Am. Chem. Soc. 2006, 128, 3928.
34. (h) Hoashi, Y.; Yabuta, T.; Yuan, P.; Miyabe, H.; Takemoto, Y. Tetrahedron 2006, 62, 365.
35. (i) Hoashi, Y.; Yabuta, T.; Takemoto, Y. Tetrahedron. Lett. 2004, 45, 9185.
36. For selected examples of phosphoric acid catalyzed domino reactions, see: (a) Rueping, M.; Antonchick, A. P. Angew. Chem., Int. Ed. 2008, 47, 5836.
37. (b) Jiang, J.; Yu, J.; Sun, X.-X.; Rao, Q.-Q.; Gong, L.-Z. Angew. Chem. Int. Ed. 2008, 47, 2458.
38. (c) Terada, M.; Machioka, K.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 10336.
39. (d) Zhou, J.; List, B. J. Am. Chem. Soc. 2007, 129, 7498.
40. (e) Akiyama, T.; Morita, H.; Fuchibe, K. J. Am. Chem. Soc. 2006, 128, 13070.
41. (f) Itoh, J.; Fuchibe, K.; Akiyama, T. Aneew. Chem., Int. Ed. 2006, 45, 4796.
42. (g) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew Chem., Int. Ed. 2006, 45, 3683.
43. (h) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
44. (i) Yang, J. W.; Hechavarria Fonseca, M. T.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2005, 44, 108.
45. For bifunctional phosphine-catalyzed domino reactions see: Meng, X.; Huang, Y.; Chen, R. Chem.-Eur. J. 2008, 14, 6852.
46. (a) Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett., 2005, 1491.
47. (b) Ma, J. A.; Cahard, D. Angew. Chem. Int. Ed. 2004, 43, 4566.
48. (c) Qi, M.-J.; Ai, T.; Shi, M.; Li, G. Tetrahedron 2008, 64, 1181.
49. (d) Shi, Y.-L.; Shi, M. Adv. Synth. Catal. 2007, 349, 2129.
50. (e) Liu, Y.-H.; Chen, L.-H.; Shi, M. Adv. Synth. Catal. 2006, 348, 973.
51. (f) Shi, M.; Chen, L.-H.; Teng, W.-D. Adv. Synth. Catal. 2005, 347, 1781.
52. (g) Matsui, K.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680.
53. (h) Balan, D.; Adolfsson, H. Tetrahedron Lett. 2003, 44, 2521.
54. (i) Shi, M.; Xu, Y.-M.; Shi, Y.-L. Chem. Eur. 2005, 11, 1794.
55. (j) Shi, M.; Xu, Y.-M. Angew. Chem. Int. Ed. 2002, 41, 4507.
56. For reviews, see: (a) Ye, L. W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140.
57. (b) Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035.
58. (c) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
59. (a) Shi, M.; Chen, L.-A.; Li, C.-Q. J. Am. Chem. Soc. 2005, 127, 3790.
60. (b) Matsui, K.; Sasai, T. H. Synlett. 2006, 761.
61. (c) Ito, K.; Nishida, K.; Gotanda, T. Tetrahedron. Lett. 2007, 48, 6147.
62. Fang, Y.-Q.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 5660.
63. Cowen, B. J.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 10988.
64. (a) Castellano, S.; Fiji, H. D. G.; Kinderman, S. S.; Watanabe, M.; de Leon, P.; Tamanoi, F.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 5843.
65. (b) Fleury-Bregeot, N.; Jean, L.; Retailleau, P.; Marinetti, A. Tetrahedron 2007, 63, 11920.
66. (c) Jean, L.; Marinetti, A. Tetrahedron Lett. 2006, 47, 2141.
67. (d) Scherer, A.; Gladysz, J. A. Tetrahedron Lett. 2006, 47, 6335.
68. (e) Zhu, X.-F.; Henry, C. E.; Kwon, O. Tetrahedron 2005, 61, 6276.
69. (f) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031.
70. (g) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836.
71. (h) Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461.
72. (a) Tran, Y. S.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 12632.
73. (b) Wurz, R. P.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 12234.
74. (c) Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716.
75. Shi, Y.-L.; Shi, M. Org. Lett. 2005, 7, 3057.
76. (a) Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819.
77. (b) Zhang, C.; Lu, X. Synlett., 1995, 645.
78. (c) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677.
79. (a) Reynaud, J.; Guilet, D.; Terreux, R.; Lussignol, M.; Walchshofer, N. Nat. Prod. Rep. 2005, 22, 504.
80. (b) Maurya, R.; Yadav, P. P. Nat. Prod. Rep. 2005, 22, 400.
81. (c) Apers, S.; Vlietinck, A.; Pieters, L. Phytochem. Rev. 2003, 2, 201.
82. Kuethe, J. T.; Wong, A.; Journet, M.; Davies, I. W. J. Org. Chem. 2005, 70, 3727, and references therein.
83. (a) Bertolini, F.; Crotti, P.; Bussolo, V. D.; Macchia, F.; Pineschi, M. J. Org. Chem. 2007, 72, 7761.
84. (b) Enders, D.; Niemeier, O.; Straverb, L. Synlett., 2006, 3399.
85. (c) Cheung, W.-H.; Sheng, S.-L.; Yu, W.-Y.; Zhou, G.-C.; Che, C.-M. Org. Lett. 2003, 5, 2535.
86. (d) Saito, H.; Oishi, H.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Org. Lett. 2002, 4, 3887.
87. Tran, Y. S.; Kwon, O. Org. Lett. 2005, 7, 4289.
88. Zhao, G.-L.; Shi, M. Org. Biomol. Chem. 2005, 3, 3686.