Highly diastereoselective and enantioselective formal [4 + 1] ylide annulation for the synthesis of optically active dihydrofurans

Journal of Organic Chemistry

Volumn 73, Issue 17, 2008, Pages 6909-6912

  Zheng, Jun Cheng ^a   Zhu, Chun Yin ^a   Sun, Xiu Li ^a   Tang, Yong ^a   Dai, Li Xin ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; SULFUR;

CHEMICAL EQUATIONS; DIHYDROFURANS; OPTICALLY ACTIVE;

SYNTHESIS (CHEMICAL);

4 ACETYL 3 (4 BROMOPHENYL) 5 METHYL 2,3 DIHYDROFURAN 2 CARBOXYLATE; CAMPHOR; ETHYL 4 ACETYL 3 (2 FURYL) 5 METHYL 2,3 DIHYDROFURAN 2 CARBOXYLATE; ETHYL 4 ACETYL 3 (2,4 DICHLOROPHENYL) 5 METHYL 2,3 DIHYDROFURAN 2 CARBOXYLATE; ETHYL 4 ACETYL 3 ETHYL 5 METHYL 2,3 DIHYDROFURAN 2 CARBOXYLATE; ETHYL 4 ACETYL 5 METHYL 3 (4 NITROPHENYL) 2,3 DIHYDROFURAN 2 CARBOXYLATE; ETHYL 4 ACETYL 5 METHYL 3 4 TOLYL 2,3 DIHYDROFURAN 2 CARBOXYLATE; ETHYL 4 ACETYL 5 METHYL 3 STYRYL 2,3 DIHYDROFURAN 2 CARBOXYLATE; ETHYLACETYL 5 METHYL 3 PHENYL 2,3 DIHYDROFURAN 2 CARBOXYLATE; FURAN DERIVATIVE; ION; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 51549085809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801135j     Document Type: Article

References (84)

1. Reviews for ylide cyclization. (a) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
2. (b) Dai, L.-X.; Hou, X.-L.; Zhou, Y.-G. Pure Appl. Chem. 1999, 71, 369.
3. (c) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 661.
4. (d) Tang, Y.; Ye, S.; Sun, X.-L. Synlett 2005, 2720.
5. (e) Gaunt, M. J.; Johansson, C. C. C. Chem. Rev. 2007, 107, 5596.
6. (f) McGarrigle, E. M.; Myers, E. L.; Illa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal, V. K. Chem. Rev. 2007, 107, 5841.
7. (a) Hayakawa, R.; Shimizu, M. Synlett 1999, 1328.
8. (b) Solladié-Cavallo, A.; Bouérat, L.; Roje, M. Tetrahedron Lett. 2000, 41, 7309.
9. (c) Ishizaki, M.; Hoshino, O. Heterocycles 2002, 57, 1399.
10. (d) Aggarwal, V. K.; Bae, I.; Lee, H.-Y.; Richardson, J.; Williams, D. T. Angew. Chem., Int. Ed. 2003, 42, 3274.
11. (e) Saito, T.; Akiba, D.; Sakairi, M.; Ishikawa, K.; Otan, T. ARKIVOC 2004, 2, 152.
12. (f) Badine, D. M.; Hebach, C.; Aggarwal, V. K. Chem. Asian J. 2006, 1, 438.
13. (a) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393.
14. (b) Solladie-Cavallo, A.; Diep-Vohuule, A.; Isarno, T. Angew. Chem., Int. Ed. 1998, 37, 1689.
15. (c) Aggarwal, V. K.; Alonso, E.; Fang, G. Y.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433.
16. (d) Lebel, H.; Marcoux, J. F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
17. (e) Papageorgiou, C. D.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2003, 42, 828.
18. (f) Liao, W. W.; Li, K.; Tang, Y. J. Am. Chem. Soc. 2003, 125, 13030.
19. (g) Papageorgiou, C. D.; Cubillo de Dios, M. A.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2004, 43, 4641.
20. (h) Bremeyer, N.; Smith, S. C.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2004, 43, 2681.
21. (i) Johansson, C. C. C.; Bremeyer, N.; Ley, S. V.; Owen, D. R.; Smith, S. C.; Gaunt, M. J. Angew. Chem., Int. Ed. 2006, 45, 6024.
22. (j) Aggarwal, V. K.; Grange, E. Chem. Eur. J. 2006, 12, 568.
23. (k) Deng, X.-M.; Cai, P.; Ye, S.; Sun, X.-L.; Liao, W.-W.; Li, K.; Tang, Y.; Wu, Y.-D.; Dai, L.-X. J. Am. Chem. Soc. 2006, 128, 9730.
24. (a) Li, A.-H.; Zhou, Y.-G.; Dai, L.-X.; Hou, X.-L.; Xia, L.-J.; Lin, L. Angew. Chem., Int. Ed. 1997, 36, 1317.
25. (b) Li, A.-H.; Zhou, Y.-G.; Dai, L.-X.; Hou, X.-L.; Xia, L.-J.; Lin, L. J. Org. Chem. 1998, 63, 4338.
26. (c) Saito, T.; Sakairi, M.; Akiba, D. Tetrahedron Lett. 2001, 42, 5451.
27. (d) Morton, D.; Pearson, D.; Field, R. A.; Stockman, R. A. Org. Lett. 2004, 6, 2377.
28. (e) Zheng, J.-C.; Liao, W.-W.; Sun, X.-X.; Sun, X.-L.; Tang, Y.; Dai, L.-X.; Deng, J.-G. Org. Lett. 2005, 7, 5789.
29. (f) Morton, D.; Field, R. A.; Stockman, R. A. Chem. Commun. 2006, 1833.
30. (g) Shen, Y.-M.; Zhao, M.-X.; Xu, J.; Shi, Y. Angew. Chem., Int. Ed. 2006, 45, 8005; and ref 3c.
31. For racemic annulations for the construction of 5-membered compounds, please see: (a) Payne, G. B. J. Org. Chem. 1967, 35, 3351.
32. (b) Clagett, M.; Gooch, A.; Graham, P.; Holy, N.; Mains, B.; Strunk, J. J. Org. Chem. 1976, 41, 4033.
33. (c) Sakakibara, T.; Sudoh, R. J. C. S. Chem. Commun. 1977, 7.
34. (d) Kumaran, G.; KulKarni, G. H. Synthesis 1995, 1545.
35. (e) Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. J. Am. Chem. Soc. 1998, 120, 9690.
36. (f) Hübner, J.; Liebscher, J.; Pätzel, M. Tetrahedron 2002, 58, 10485.
37. (g) Cao, W.; Chen, G.; Chen, J.; Chen, R. Synth. Commun. 2005, 35, 527.
38. (h) Yang, Z.; Fan, M.; Mu, R.; Liu, W.; Liang, Y. Tetradedron 2005, 61, 9140.
39. (i) Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F.; Spiga, M. Org. Lett. 2005, 7, 4565.
40. (a) Jiang, Y.; Ma, D. Tetrahedron: Asymmetry 2002, 13, 1033.
41. (b) Zhu, C.-Y.; Deng, X.-M.; Sun, X.-L.; Zheng, J.-C.; Tang, Y. Chem. Commun. 2008, 738.
42. (c) Zhu, C.-Y.; Sun, X.-L.; Deng, X.-M.; Zheng, J.-C.; Tang, Y. Tetrahedron 2008, 5583.
43. For a review, please see: Sun, X. L.; Tang, Y. Acc. Chem. Res. 2008, 41, DOI: 10.1021/ar800108z.
44. For recent work, please see: (a) Ye, S.; Huang, Z. Z.; Xia, C. A.; Tang, Y.; Dai, L. X. J. Am. Chem. Soc. 2002, 124, 2432.
45. (b) Liao, W. W.; Deng, X. M.; Tang, Y. Chem. Commun. 2004, 1516.
46. (c) Zheng, J.-C.; Liao, W.-W.; Tang, Y.; Sun, X.-L.; Dai, L. X. J. Am. Chem. Soc. 2005, 127, 12222.
47. (d) Ye, L.-W.; Sun, X.-L.; Wang, Q.-G.; Tang, Y. Angew. Chem., Int. Ed. 2007, 46, 5951.
48. (e) Cao, P.; Li, C.-Y.; Kang, Y.-B.; Xie, Z.; Sun, X.-L.; Tang, Y. J. Org. Chem. 2007, 72, 6628.
49. (f) Li, C.-Y.; Wang, X.-B.; Sun, X.-L.; Tang, Y.; Zheng, J.-C.; Xu, Z.-H.; Zhou, Y.-G.; Dai, L.-X. J. Am. Chem. Soc. 2007, 129, 1494.
50. Leading references for the enantioselective synthesis of 5- or 6-membered rings via ylide route other than formal [4 + 1] annulation: (a) Koep, S.; Gais, H.-J.; Raabe, G. J. Am. Chem. Soc. 2003, 125, 13243.
51. (b) Gais, H.-J.; Reddy, L. R.; Babu, G. S.; Raabe, G. J. Am. Chem. Soc. 2004, 126, 4859.
52. (c) Schomaker, J. M.; Pulgam, V. R.; Borhan, B. J. Am. Chem. Soc. 2004, 126, 13600.
53. (d) Kumarn, S.; Shaw, D. M.; Longbottom, D. A.; Ley, S. V. Org. Lett. 2005, 7, 4189.
54. (e) Kumarn, S.; Shaw, D. M.; Ley, S. V. Chem. Commun. 2006, 3211.
55. (f) Tiwari, S. K.; Gais, H.-J.; Lindenmaier, A.; Babu, G. S.; Raabe, G.; Reddy, L. R.; Köhler, F.; Günter, M.; Koep, S.; Iska, V. B. R. J. Am. Chem. Soc. 2006, 128, 7360.
56. (g) Kokotos, C. G.; Aggarwal, V. K. Chem. Commun. 2006, 2156.
57. (h) Unthank, M. G.; Hussain, N.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2006, 45, 7066.
58. (i) Kokotos, C. G.; Aggarwal, V. K. Org. Lett. 2007, 9, 2099.
59. (j) Schomaker, J. M.; Bhattacharjee, S.; Yan, J.; Borhan, B. J. Am. Chem. Soc. 2007, 129, 1996.
60. Leading references for the enantioselective synthesis of dihydrofurans: (a) Daivs, H. M.L.; Ahmed, G.; Calvo, R. L.; Churchill, M. R.; Churchill, D. G. J. Org. Chem. 1998, 63, 2641.
61. (b) Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. J. Am. Chem. Soc. 2001, 123, 12095.
62. (c) Garzino, F.; Méou, A.; Brun, P. Eur. J. Org. Chem. 2003, 1410.
63. (d) Xia, W.; Yang, C.; Patrick, B. O.; Scheffer, J. R.; Scott, C. J. Am. Chem. Soc. 2005, 127, 2725.
64. (e) Calter, M. A.; Phillips, R. M.; Flaschenriem, C. J. Am. Chem. Soc. 2005, 127, 14566.
65. (f) Bowman, R. K.; Johnson, J. S. Org. Lett. 2006, 8, 573.
66. (g) Son, S.; Fu, G. C. J. Am. Chem. Soc. 2007, 129, 1046.
67. (a) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 217.
68. (b) Merrit, A. T.; Ley, S. V. Nat. Prod. Rep. 1992, 9, 243.
69. (c) Mortensen, D. S.; Rodriguez, A. L.; Carlson, K. E.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. J. Med. Chem. 2001, 44, 3838.
70. (d) Kilroy, T. G.; O'Sullivan, T. P.; Guiry, P. J. Eur. J. Org. Chem. 2005, 4929.
71. (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
72. (b) Faul, M. M.; Huff, B. E. Chem. Rev. 2000, 100, 2407.
73. (c) Garzino, F.; Meou, A.; Brun, P. Synthesis 2003, 598.
74. (d) Pettigrew, J. D.; Wilson, P. D. Org. Lett. 2006, 8, 1427.
75. For applications of camphor-derived sulfonium salts in organic synthesis, please see: (a) Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489.
76. (b) Zhou, Y.-G.; Hou, X.-L.; Dai, L.-X.; Xia, L.-J.; Tang, M.-H. J. Chem. Soc., Perkin Trans. 1 1999, 77.
77. (c) Aggarwal, V. K.; Hynd, G.; Picoul, W.; Vasse, J. L.; Winn, C. L. J. Am. Chem. Soc. 2002, 124, 9964.
78. (d) Huang, K.; Huang, Z.-Z. Synlett 2005, 1621.
79. (e) Aggarwal, V. K.; Charmant, J. P. H.; Fuentes, D.; Harvey, J. N.; Hynd, G.; Ohara, D.; Picoul, W.; Robiette, R.; Smith, C.; Vasse, J. L.; Winn, C. L. J. Am. Chem. Soc. 2006, 128, 2105.
80. (f) Deng, X.-M.; Cai, P.; Ye, S.; Sun, X.-L.; Liao, W.-W.; Li, K.; Tang, Y.; Wu, Y.-D.; Dai, L.-X. J. Am. Chem. Soc. 2006, 128, 9730.
81. (g) Wang, Q.-G.; Deng, X.-M.; Zhu, B.-H.; Ye, L.-W.; Sun, X.-L.; Li, C.-Y.; Zhu, C.-Y.; Shen, Q.; Tang, Y. J. Am. Chem. Soc. 2008, 130, 5408.
82. For details, please see the Supporting Information.
83. 60-70% sulfide 6 was recovered.
84. For the synthesis of sulfide 6 see: Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489.