Telluronium and sulfonium ylides for organic transformation

Synlett

Volumn , Issue 18, 2005, Pages 2720-2730

  Tang, Yong ^a   Ye, Song ^b,c   Sun, Xiu Li ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b INSTITUTE OF CHEMISTRY   (China)

^c INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

Aziridination; Catalytic Wittig type reaction; Cyclopropanation; Epoxidation; Telluronium ylide

Indexed keywords

ALKENE; ALKENE DERIVATIVE; ALLYL COMPOUND; AZIRIDINE; AZIRIDINE DERIVATIVE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; EPOXIDE; GLYCOLIC ACID DERIVATIVE; ORGANOTELLURIUM DERIVATIVE; SULFONIUM DERIVATIVE; TELLURIUM DERIVATIVE; TETRAHYDROTHIOPHENE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; BIOTRANSFORMATION; CATALYSIS; CHIRALITY; CYCLIZATION; CYCLOPROPANATION; DERIVATIZATION; DIASTEREOISOMER; EPOXIDATION; LABORATORY; OLEFINATION; ORGANIC CHEMISTRY; PROCESS DEVELOPMENT; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; WITTIG REACTION;

EID: 27844449972     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918929     Document Type: Article

References (62)

1. Wittig, G.; Geissler, G. Justus Liebigs Ann. Chem. 1953, 580, 44.
2. (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
3. (b) Kolodiazhnyi, O. I. Phosphorus Ylides: Chemistry and Application in Organic Synthesis; Wiley-VCH: New York, 1999.
4. (c) Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 2341.
5. (d) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
6. (e) Tang, Y.; Ye, S.; Huang, Z.-Z.; Huang, Y.-Z. Heteroat. Chem. 2002, 13, 463.
7. Trost, B. M. Science 1991, 254, 1471.
8. Shi, L.; Wang, W.; Wang, Y.; Huang, Y.-Z. J. Org. Chem. 1989, 54, 2027.
9. Huang, Y.-Z.; Shi, L.-L.; Li, S.-W.; Wen, X.-Q. J. Chem. Soc., Perkin Trans. 1 1989, 2397.
10. Li, S.-W. PhD Thesis; Shanghai Institute of Organic Chemistry: Shanghai, 1990.
11. PEG is being developed as an excellent matrix for organic synthesis: Wentworth, P.; Janda, K. D. Chem. Commun. 1999, 1917.
12. Maynard, H. D.; Grubbs, R. H. Macromolecules 1999, 32, 6917.
13. (a) Huang, Z.-Z.; Ye, S.; Xia, W.; Tang, Y. Chem. Commun. 2001, 1384.
14. (b) Huang, Z.-Z.; Ye, S.; Xia, W.; Yu, Y.-H.; Tang, Y. J. Org. Chem. 2002, 67, 3096.
15. Li, K.; Ran, L.; Yu, Y.-H.; Tang, Y. J. Org. Chem. 2004, 69, 3986.
16. Huang, Z.-Z.; Tang, Y. J. Org. Chem. 2002, 67, 5320.
17. (a) Henrick, C. A. In Pyrethroids in Agrochemicals from Natural Products; Godfrey, C. R. A., Ed.; Marcel Dekker: New York, 1995, 147-213.
18. (b) Faust, R. Angew. Chem. Int. Ed. 2001, 40, 2251.
19. (c) Salaün, J. Top. Curr. Chem. 2000, 207, 1.
20. (d) Pietruszka, J. Chem. Rev. 2003, 103, 1051.
21. (e) Wessjohann, L. A.; Brandt, W. Chem. Rev. 2003, 103, 1625.
22. (a) Baldwin, J. E. Chem. Rev. 2003, 103, 1197.
23. (b) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
24. Wong, H. N. C.; Hon, M.-Y.; Tse, C-W.; Yip, Y.-C; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
25. (a) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
26. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
27. (c) Salaün, J. Chem. Rev. 1989, 89, 1247.
28. Osuka, A.; Suzuki, H. Tetrahedron Lett. 1983, 24, 5109.
29. (a) Zhou, Z.-L.; Sun, Y.-S.; Shi, L.-L.; Huang, Y.-Z. J. Chem. Soc., Chem. Commun. 1990, 1439.
30. (b) Zhou, Z.-L.; Huang, Y.-Z.; Shi, L.-L.; Hu, J. J. Org. Chem. 1992, 57, 6598.
31. Huang, Y.-Z.; Tang, Y.; Zhou, Z.-L.; Huang, J.-L. J. Chem. Soc., Chem. Commun. 1993, 7.
32. Tang, Y.; Chi, Z.-F.; Huang, Y.-Z.; Dai, L.-X.; Yu, Y.-H. Tetrahedron 1996, 52, 8747.
33. Huang, Y.-Z.; Tang, Y.; Zhou, Z.-L.; Xia, W.; Shi, L.-P. J. Chem. Soc., Perkin Trans. 1 1994, 893.
34. Tang, Y.; Huang, Y.-Z.; Dai, L.-X.; Chi, Z.-F.; Shi, L.-P. J. Org. Chem. 1996, 61, 5762.
35. Ye, S.; Yuan, L.; Huang, Z.-Z.; Tang, Y.; Dai, L.-X. J. Org. Chem. 2000, 65, 6257.
36. Tang, Y.; Huang, Y.-Z.; Dai, L.-X.; Sun, J.; Xia, W. J. Org. Chem. 1997, 62, 954.
37. (a) Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489.
38. (b) Ye, S.; Huang, Z.-Z.; Xia, C.-A.; Tang, Y.; Dai, L.-X. J. Am. Chem. Soc. 2002, 724, 2432.
39. Ye, S.; Tang, Y.; Dai, L.-X. J. Org. Chem. 2001, 66, 5717.
40. Liao, W.-W.; Li, K.; Tang, Y. J. Am. Chem. Soc. 2003, 125, 13030.
41. (a) Hudlicky, T.; Reed, J. W. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, 899.
42. (b) Lautens, M.; Quellet, S. G.; Raeppel, S. Angew. Chem. Int. Ed. 2000, 39, 4079.
43. (c) Trost, B. M.; Jiang, C. J. Am. Chem. Soc. 2001, 123, 12907.
44. Zhou, Z.-L.; Shi, L.-L.; Huang, Y.-Z. Tetrahedron Lett. 1990, 31, 7657.
45. Zhou, Y.-G.; Li, A.-H.; Dai, L.-X.; Hou, X.-L. Chem. Commun. 1996, 1353.
46. Li, K.; Huang, Z.-Z.; Tang, Y. Tetrahedron Lett. 2003, 44, 4137.
47. Johnson, A. W.; LaCount, R. B. Chem. Ind. (London) 1958, 1440.
48. Li, K.; Deng, X.-M.; Tang, Y. Chem. Commun. 2003, 2074.
49. (a) Zwanenburg, B.; ten Holte, P. Stereoselective Heterocyclic Synthesis III, In Topics in Current Chemistry, Vol. 216; Metz, P., Ed.; Springer: Berlin, 2001, 93.
50. (b) Remers, W. A.; Iyengar, B. S. Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G.; Ohno, M., Eds.; Springer: Berlin, 1990, 415.
51. (a) Mueller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
52. (b) Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
53. (a) Li, A. H.; Dai, L. X.; Hou, X. L. Chem. Commun. 1996, 491.
54. (b) Li, A. H.; Dai, L. X.; Hou, X. L. J. Chem. Soc., Perkin Trans. 1 1996, 867.
55. (c) Li, A. H.; Dai, L. X.; Hou, X. L.; Chen, M. B. J. Org. Chem. 1996, 41, 4641.
56. (d) Li, A. H.; Dai, L. X.; Hou, X. L. J. Chem. Soc., Perkin Trans. 1 1996, 2725.
57. (a) Hou, X. L.; Yang, X. F.; Dai, L. X.; Chen, X. F. Chem. Commun. 1998, 747.
58. (b) Yang, X. F.; Zhang, M. J.; Hou, X. L.; Dai, L. X. J. Org. Chem. 2002, 67, 8097.
59. (c) Wang, D. K.; Dai, L. X.; Hou, X. L. Chem. Commun. 1997, 1231.
60. (a) Aggarwal, V. K.; Charmant, J. P. H.; Ciampi, C.; Hornby, J. M.; O'Brien, C. J.; Hynd, G.; Parsons, R. J. Chem. Soc., Perkin Trans. 1 2001, 3159.
61. (b) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem. Int. Ed. 2001, 40, 1433.
62. Liao, W.-W.; Deng, X.-M.; Tang, Y. Chem. Commun. 2004, 1516.