Formal [4+1] cycloaddition of camphor-derived sulfonium salts with aldimines: Enantioselective synthesis of 2,3-dihydrobenzofurans

Tetrahedron

Volumn 69, Issue 19, 2013, Pages 3810-3816

  Cheng, Ying ^a   Hu, Xiao Qiang ^a   Gao, Shuang ^a   Lu, Liang Qiu ^a   Chen, Jia Rong ^a   Xiao, Wen Jing ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

2,3 Dihydrobenzofurans; Aldimines; Cycloaddition; Sulfonium salts

Indexed keywords

CAMPHOR; DIHYDROBENZOFURAN DERIVATIVE; SULFONIUM DERIVATIVE;

ANNULATION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CRYSTAL STRUCTURE; CYCLOADDITION; CYCLOPROPANATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

DRYOBALANOPS;

EID: 84875926454     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.03.059     Document Type: Article

References (45)

1. M. Sefkow Synthesis 2003 2595 2625
2. S. Garcia-Muñoz, L. Jiménez-González, M. Álvarez-Corral, M. Muñoz-Dorado, and I. Rodriguez-Garcia Synlett 2005 3011 3013
3. M. Okazaki, and Y. Shuto Biosci. Biotechnol. Biochem. 65 2001 1134 1140
4. R.S. Ward Nat. Prod. Rep. 16 1999 75 96
5. M.S.M. Yuen, F. Xue, T.C.W. Mak, and H.N.C. Wong Tetrahedron 54 1998 12429 12444
6. K. Komiyama, S. Funayama, Y. Anraku, M. Ishibashi, Y. Takahashi, and S. Omura J. Antibiot. 43 1990 247 252
7. M. Ishibashi, S. Funayama, Y. Anraku, K. Komiyama, and S. Omura J. Antibiot. 44 1991 390 395
8. T. Saito, T. Suzuki, M. Morimoto, C. Akiyama, T. Ochiai, K. Takeuchi, T. Matsumoto, and K. Suzuki J. Am. Chem. Soc. 120 1998 11633 11644
9. J. Meng, T. Jiang, H.A. Bhatti, B.S. Siddiqui, S. Dixon, and J.D. Kilburn Org. Biomol. Chem. 8 2010 107 113
10. J.P. Nandy, B. Rakic, B.V.N.B. Sarma, N. Babu, M. Lefrance, G.D. Enright, D.M. Leek, K. Daniel, L.A. Sabourin, and P. Arya Org. Lett. 10 2008 1143 1146
11. M.A. Calter, and N. Li Org. Lett. 13 2011 3686 3689
12. S. Antus, T. Kurtán, L. Juhász, L. Kiss, M. Hollósi, and Z.S. Májer Chirality 13 2001 493 506
13. S.M.O. Van Dyck, G.L.F. Lemière, T.H.M. Jonckers, R. Dommisse, L. Pieters, and V. Buss Tetrahedron: Asymmetry 12 2001 785 789
14. L. Juhász, J. Visy, M. Simonyi, K. Krohn, and S. Antus Tetrahedron: Asymmetry 13 2002 1219 1222
15. T. Itoh, K. Kawai, S. Hayase, and H. Ohara Tetrahedron Lett. 44 2003 4081 4084
16. E. Bolzacchini, G. Brunow, S. Meinardi, M. Orlandi, B. Rindone, P. Rummakko, and H. Setala Tetrahedron Lett. 39 1998 3291 3294
17. M.G.N. Russell, R. Baker, and J.L. Castro Tetrahedron Lett. 40 1999 8667 8670
18. M. Orlandi, B. Rindone, G. Molteni, P. Rummakko, and G. Brunow Tetrahedron 57 2001 371 378
19. W. Kurosawa, H. Kobayashi, T. Kan, and T. Fukuyama Tetrahedron 60 2004 9615 9628
20. T.A. Engler, M.A. Letavic, R. Iyengar, K.O. LaTessa, and J.P. Reddy J. Org. Chem. 64 1999 2391 2405
21. H.M.L. Davies, M.V.A. Grazini, and E. Aouad Org. Lett. 3 2001 1475 1477
22. H. Saito, H. Oishi, S. Kitagaki, S. Nakamura, M. Anada, and S. Hashimoto Org. Lett. 4 2002 3887 3890
23. L. Jiménez-González, S. Garcia-Muñoz, M. Álvarez-Corral, M. Muñoz-Dorado, and I. Rodriguez-Garcia Chem. - Eur. J. 12 2006 8762 8769
24. Ł. Albrecht, L.K. Ransborg, V. Lauridsen, M. Overgaard, T. Zweifel, and K.A. Ju̧rgensen Angew. Chem., Int. Ed. 50 2011 12496 12500
25. L.-Q. Lu, Y.-J. Cao, X.-P. Liu, J. An, C.-J. Yao, Z.-H. Ming, and W.-J. Xiao J. Am. Chem. Soc. 130 2008 6946 6948
26. L.-Q. Lu, F. Li, J. An, J.-J. Zhang, X.-L. An, Q.-L. Hua, and W.-J. Xiao Angew. Chem., Int. Ed. 48 2009 9542 9545
27. L.-Q. Lu, J.-J. Zhang, F. Li, Y. Cheng, J. An, J.-R. Chen, and W.-J. Xiao Angew. Chem., Int. Ed. 49 2010 4495 4498
28. L.-Q. Lu, F. Li, J. An, Y. Cheng, J.-R. Chen, and W.-J. Xiao Chem. - Eur. J. 18 2012 4073 4079
29. L.-Q. Lu, Z.-H. Ming, J. An, C. Li, J.-R. Chen, and W.-J. Xiao J. Org. Chem. 77 2012 1072 1080
30. V.K. Aggarwal, and C.L. Winn Acc. Chem. Res. 37 2004 611 620
31. E.M. McGarrigle, E.L. Myers, O. Illa, M.A. Shaw, S.L. Riches, and V.K. Aggarwal Chem. Rev. 107 2007 5841 5883
32. X.-L. Sun, and Y. Tang Acc. Chem. Res. 41 2008 937 948
33. L.-Q. Lu, J.-R. Chen, and W.-J. Xiao Acc. Chem. Res. 45 2012 1278 1293
34. Y. Cheng, J. An, L.-Q. Lu, L. Luo, Z.-Y. Wang, J.-R. Chen, and W.-J. Xiao J. Org. Chem. 76 2011 281 284
35. Q.-Q. Yang, C. Xiao, L.-Q. Lu, J. An, F. Tan, B.-J. Li, and W.-J. Xiao Angew. Chem., Int. Ed. 51 2012 9137 9140
36. P.-Z. Xie, L.-Y. Wang, L.-H. Yang, E.-Q. Li, J.-Z. Ma, Y. Huang, and R.-Y. Chen J. Org. Chem. 76 2011 7699 7705
37. J.-R. Chen, W.-R. Dong, M. Candy, F.-F. Pan, M. Jorres, and C. Bolm J. Am. Chem. Soc. 134 2012 6924 6927
38. O.A. Attanasi, L. De Crescentini, G. Favi, P. Filippone, F. Mantellini, F.R. Perrulli, and S. Santeusanio Eur. J. Org. Chem. 2009 3109 3127
39. R.J. Goodridge, T.W. Hambley, R.K. Haynes, and D.D. Ridley J. Org. Chem. 53 1988 2881 2889
40. A.-H. Li, L.-X. Dai, X.-L. Hou, Y.-Z. Huang, and F.-W. Li J. Org. Chem. 61 1996 489 493
41. K. Fujiki, N. Tanifuji, Y. Sasaki, and T. Yokoyama Synthesis 2002 343 348
42. V.K. Aggarwal, G. Hynd, W. Picoul, and J. Vasse J. Am. Chem. Soc. 124 2002 9964 9965
43. V.K. Aggarwal, J.P.H. Charmant, D. Fuentes, J.N. Harvey, G. Hynd, D. Ohara, W. Picoul, R. Robiette, C. Smith, J. Vasse, and C. Winn J. Am. Chem. Soc. 128 2006 2105 2114 and references therein
44. L.C. Da Silva-Filho, V. Lacerda Júnior, M.G. Constantino, and G.V.J. Da Silva Synthesis 2008 2527 2536
45. A.J. Speziale, C.C. Tung, K.W. Ratts, and A. Yao J. Am. Chem. Soc. 87 1965 3460 3462