Phosphine-catalyzed intramolecular formal [3+2] cycloaddition for highly diastereoselective synthesis of bicyclo[n.3.0] compounds

Angewandte Chemie - International Edition

Volumn 46, Issue 31, 2007, Pages 5951-5954

  Ye, Long Wu ^a   Sun, Xiu Li ^a   Wang, Qing Gang ^a   Tang, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Annulation; Bicyclic compounds; Diastereoselectivity; Homogeneous catalysis; Intramolecular reactions

Indexed keywords

CATALYSIS; MOLECULAR STRUCTURE; STEREOSELECTIVITY;

ANNULATION; BICYCLIC COMPOUNDS; DIASTEREOSELECTIVITY; HOMOGENEOUS CATALYSIS;

AROMATIC COMPOUNDS;

EID: 34547781801     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701460     Document Type: Article

References (77)

1. For reviews on ylide epoxidation, see: a) V. K. Aggarwal, C. L. Winn, Acc. Chem. Res. 2004, 37, 611;
2. for recent examples, see: b) M. Davoust, J.-F. Brière, P. Metzner, Org. Biomol. Chem. 2006, 4, 3048;
3. c) V. K. Aggarwal, J. P. H. Charmant, D. Fuentes, J. N. Harvey, G. Hynd, D. Ohara, W. Picoul, R. Robiette, C. Smith, J.-L. Vasse, C. L. Winn, J. Am. Chem. Soc. 2006, 128, 2105;
4. d) D. M. Badine, C. Hebach, V. K. Aggarwal, Chem. Asian J. 2006, 1, 438;
5. e) M. Davoust, J.-F. Brière, P.-A. Jaffrès, P. Metzner, J. Org. Chem. 2005, 70, 4166;
6. f) W.-H. Ou, Z.-Z. Huang, Synthesis 2005, 2857;
7. g) K. Li, X.-M. Deng, Y. Tang, Chem. Commun. 2003, 2074;
8. h) J. Zanardi, D. Lamazure, S. Minière, V. Reboul, P. Metzner, J. Org. Chem. 2002, 67, 9083.
9. For reviews on ylide cyclopropanation, see: a) S. Ye, Y. Tang, X.-L. Sun, Synlett 2005, 2720;
10. b) H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977;
11. c) P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905;
12. d) A.-H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341;
13. for recent examples, see: e) C. C. C. Johansson, N. Bremeyer, S. V. Ley, D. R. Owen, S. C. Smith, M. J. Gaunt, Angew. Chem. 2006, 118, 6170;
14. Angew. Chem. Int. Ed. 2006, 45, 6024;
15. f) V. K. Aggarwal, E. Grange, Chem. Eur. J. 2006, 12, 568;
16. g) R. K. Kunz, D. W. C. Macmillan, J. Am. Chem. Soc. 2005, 127, 3240;
17. h) K. Huang, Z.-Z. Huang, Synlett 2005, 1621;
18. i) M. Mikoajczyk, W. H. Midura, E. Michedkina, A. D. Filipczak, M. W. Wieczorek, Helv. Chim. Acta 2005, 88, 1769;
19. j) C. D. Papageorgiou, M. A. Cubillo de Dios, S. V. Ley, M. J. Gaunt, Angew. Chem. 2004, 116, 4741;
20. Angew. Chem. Int. Ed. 2004, 43, 4641;
21. k) N. Bremeyer, S. C. Smith, S. V. Ley, M. J. Gaunt, Angew. Chem. 2004, 116, 2735;
22. Angew. Chem. Int. Ed. 2004, 43, 2681;
23. l) C. D. Papageorgiou, S. V. Ley, M.J. Gaunt, Angew. Chem. 2003, 115, 852;
24. Angew. Chem. Int. Ed. 2003, 42, 828.
25. For reviews on ylide aziridination, see reference [2a,d]; for recent examples, see: a) R. Robiette, J. Org. Chem. 2006, 71, 2726;
26. b) D. Morton, D. Pearson, R. A. Field, R. A. Stockman, Chem. Commun. 2006, 1833;
27. c) J.-C. Zheng, W.-W. Liao, X.-X. Sun, X.-L. Sun, Y. Tang, L.-X. Dai, J. G. Deng, Org. Lett. 2005, 7, 5789;
28. d) D. Morton, D. Pearson, R. A. Field, R. A. Stockman, Org. Lett. 2004, 6, 2377;
29. e) W.-W. Liao, X.-M. Deng, Y. Tang, Chem. Commun. 2004, 1516;
30. f) V. K. Aggarwal, E. Alonso, G. Fang, M. Ferrar, G. Hynd, M. Porcelloni, Angew. Chem. 2001, 113, 1482;
31. Angew. Chem. Int. Ed. 2001, 40, 1433;
32. g) A.-H. Li, Y-G. Zhou, L.-X. Dai, X.-L. Hou, L.-J. Xia, L. Lin, Angew. Chem. 1997, 109, 1375;
33. Angew. Chem. Int. Ed. Engl. 1997, 36, 1317.
34. a) X. Lu, Z. Lu, X. Zhang, Tetrahedron 2006, 62, 457;
35. b) Y. Du, J. Feng, X. Lu, Org. Lett. 2005, 7, 1987;
36. c) Y. Du, X. Lu, C. Zhang, Angew. Chem. 2003, 115, 1065;
37. Angew. Chem. Int. Ed. 2003, 42, 1035;
38. d) Y. Du, X. Lu, J. Org. Chem. 2003, 68, 6463;
39. e) C. Lu, X. Lu, Org. Lett. 2002, 4, 4677;
40. f) Y. Du, X. Lu, Y. Yu, J. Org. Chem. 2002, 67, 8901;
41. g) X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535.
42. a) J.-C. Wang, S.-S. Ng, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 3682;
43. b) J.-C. Wang, M. J. Krische, Angew. Chem. 2003, 115, 6035;
44. Angew. Chem. Int. Ed. 2003, 42, 5855.
45. a) J. E. Wilson, G. C. Fu, Angew. Chem. 2006, 118, 1454;
46. Angew. Chem. Int. Ed. 2006, 45, 1426;
47. b) R. P. Wurz, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 12234;
48. c) G. Zhu, Z. Chen, Q. Jiang, D. Xiao, P. Cao, X. Zhang, J. Am. Chem. Soc. 1997, 119, 3836.
49. a) C. G. Kokotos, V. K. Aggarwal, Chem. Commun. 2006, 2156;
50. b) M. G. Unthank, N. Hussain, V. K. Aggarwal, Angew. Chem. 2006, 118, 7224;
51. Angew. Chem. Int. Ed. 2006, 45, 7066.
52. a) C.-Y. Li, X.-B. Wang, X.-L. Sun, Y. Tang, J.-C. Zheng, Z.-H. Xu, Y.-G. Zhou, L.-X. Dai, J. Am. Chem. Soc. 2007, 129, 1494;
53. b) X.-M. Deng, P. Cai, S. Ye, X.-L. Sun, W.-W. Liao, K. Li, Y. Tang, Y.-D. Wu, L.-X. Dai, J. Am. Chem. Soc. 2006, 128, 9730;
54. c) J.-C. Zheng, W.-W. Liao, Y. Tang, X.-L. Sun, L.-X. Dai, J. Am. Chem. Soc. 2005, 127, 12222;
55. d) W.-W. Liao, K. Li, Y. Tang, J. Am. Chem. Soc. 2003, 125, 13030;
56. e) S. Ye, Z.-Z. Huang, Y. Tang, L.-X. Dai, J. Am. Chem. Soc. 2002, 124, 2432.
57. a) L.-W. Ye, X.-L. Sun, C.-Y. Zhu, Y. Tang, Org. Lett. 2006, 8, 3853;
58. b) L.-W. Ye, X.-L. Sun, C.-Y. Li, Y. Tang, J. Org. Chem. 2007, 72, 1335.
59. For reviews on phosphine-mediated annulation reactions, see: a) J. L. Methot, W. R. Roush, Adv. Synth. Catal. 2004, 346, 1035;
60. b) X. Lu, Y. Du, C. Lu, Pure. Appl. Chem. 2005, 77, 1985;
61. for recent examples, see: c) N. T. McDougal, S. E. Schaus, Angew. Chem. 2006, 118, 3189;
62. Angew. Chem. Int. Ed. 2006, 45, 3117;
63. d) T. Dudding, O. Kwon, E. Mercier, Org. Lett. 2006, 8, 3643;
64. e) M. E. Krafft, J. A. Wright, Chem. Commun. 2006, 2977;
65. f) M. E. Krafft, T. F. N. Haxell, J. Am. Chem. Soc. 2005, 127, 10168;
66. g) M.E. Krafft, K. A. Seibert, T.F.N. Haxell, C. Hirosawa, Chem. Commun. 2005, 5772;
67. h) R. K. Thalji, W. R. Roush, J. Am. Chem. Soc. 2005, 127, 16778;
68. i) Y. S. Tran, O. Kwon, Org. Lett. 2005, 7, 4289;
69. j) X.-F. Zhu, A.-P. Schaffner, R. C. Li, O. Kwon, Org. Lett. 2005, I, 2977;
70. k) X.-F. Zhu, C. E. Henry, J. Wang, T. Dudding, O. Kwon, Org. Lett. 2005, 7, 1387;
71. l) C.-K. Jung, J.-C. Wang, M. J. Krische, J. Am. Chem. Soc. 2004, 126, 4118.
72. 1H COSY spectra of compounds 4b and 6a are available in the Supporting Information.
73. a) K. H. Park, H. Rapoport, J. Org. Chem. 1994, 59, 394;
74. b) A. Kuhl, W. Kreiser, Helv. Chim. Acta 1998, 81, 2264.
75. T. Uyehara, N. Shida, Y. Yamamoto, J. Org. Chem. 1992, 57, 3139.
76. J. G. Urones, N. M. Garrido, X. D. Díez, S. H. Dominguez, S. G. Davies, Tetrahedron: Asymmetry 1997, 8, 2683.
77. CCDC-644663 (4g'), -644662 (6j), and -644664 (9) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.