Controllable Diastereoselective Cyclopropanation. Enantioselective Synthesis of Vinylcyclopropanes via Chiral Telluronium Ylides

Journal of the American Chemical Society

Volumn 125, Issue 43, 2003, Pages 13030-13031

  Liao, Wei Wei ^a   Li, Kai ^a   Tang, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE; PHOSPHONAMIDE; PHOSPHONIC ACID DERIVATIVE; TELLURONIUM YLIDE; UNCLASSIFIED DRUG; VINYLCYCLOPROPANE;

ARTICLE; CATALYSIS; CHIRALITY; CYCLOPROPANATION; DIASTEREOISOMER; ENANTIOMER; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

ALKENES; CYCLIZATION; CYCLOPROPANES; STEREOISOMERISM; TELLURIUM; VINYL COMPOUNDS;

EID: 0142214626     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036254c     Document Type: Article

References (49)

1. (a) Henrick, C. A. In Pyrethroids in Agrochemicals from Natural Products; Godfrey, C. R. A., Ed.; Marcel Dekker: New York, 1995; pp 147-213.
2. (b) Faust, R. Angew. Chem., Int. Ed. 2001, 40, 2251.
3. (c) Salaün, J. Top. Curr. Chem. 2000, 207, 1.
4. (d) Pietruszka, J. Chem. Rev. 2003, 103, 1051.
5. (e) Wessjohann, L. A.; Brandt, W. Chem. Rev. 2003, 103, 1625.
6. (a) Baldwin, J. E. Chem. Rev. 2003, 103, 1197.
7. (b) Nonhebel, D. C. Chem. Soc. Rev. 1993, 22, 347.
8. (c) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
9. (d) Davies, H. M. L. Tetrahedron 1993, 49, 5203.
10. (e) Trost, B. M.; Yasukata, T. J. Am. Chem. Soc. 2001, 123, 7162.
11. (f) Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123, 179.
12. (g) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
13. (a) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
14. (b) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
15. (b) Salaün, J. Chem. Rev. 1989, 89, 1247.
16. (c) Majumdar, S.; Meijere, A.; Marek, I. Synlett. 2002, 423.
17. (d) Cheng, D.; Knox, K. R.; Cohen, T. J. Am. Chem. Soc. 2000, 122, 412.
18. (e) Ma, S.; Zhao, S. Org. Lett. 2000, 2, 2495.
19. (a) Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1977, 18, 2599.
20. (b) Aratani, T. Pure Appl. Chem. 1985, 57, 1839.
21. (c) Bachmann, S.; Furler, M.; Mezzetti, A. Organometallics 2001, 20, 2102.
22. (d) Lowenthal, R. E.; Masamune, S. Tetrahedron. Lett. 1991, 32, 7373.
23. (e) Böhm, C.; Schinnerl, M.; Bubert, C.; Zabel, M.; Labahn, T.; Parisini, E.; Reiser, O. Eur. J. Org. Chem. 2000, 2955.
24. (f) Davies, H. M. L.; Huby, N. J. S.; Cantrell, W. R.; Olive, J. L. J. Am. Chem. Soc. 1993, 115, 9468.
25. (g) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
26. (h) Davies, H. M. L.; Doan, B. D. J. Org. Chem. 1999, 64, 8501.
27. (i) Davies, H. M. L.; Hutcheson, D. K. Tetrahedron Lett. 1993, 34, 7243.
28. (j) Davies, H. M. L.; Panaro, S. A. Tetrahedron Lett. 1999, 40, 5287.
29. (k) Böhm, C.; Reiser, O. Org. Lett. 2001, 3, 1315.
30. (l) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967.
31. (m) Davies, H. M. L.; Calvo, R. L.; Townsend, R. J.; Ren, P.; Churchill, R. M. J. Org. Chem. 2000, 65, 4261.
32. (a) Nagasawa, T.; Handa, Y.; Onoguchi, Y.; Ohba, S.; Suzuki, K. Synlett 1995, 739.
33. (b) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. J.; Yuan, H. J. Am. Chem. Soc. 2001, 123, 2964.
34. Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393.
35. Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433.
36. Ye, S.; Huang, Z.-Z.; Xia, C.-A.; Tang, Y.; Dai, L.-X. J. Am. Chem. Soc. 2002, 11, 2432.
37. (a) Julienne, K.; Metzner, P. J. Org. Chem. 1998, 63, 4532.
38. (b) Zanardi, J.; Lamazure, D.; Miniére, S.; Reboul, V.; Metzner, P. J. Org. Chem. 2002, 67, 9083.
39. The telluronium chemistry is well studied. For reviews, please see: (a) Irgolic, K. J. The Organic Chemistry of Tellurium; Gordon and Breach: London, 1974.
40. (b) Engman, L. Acc. Chem. Res. 1985, 18, 274.
41. (c) Petragnani, N.; Comasseto, J. V. Synthesis 1986, 1.
42. (d) Petragnani, N.; Comasseto, J. V. Synthesis 1991, 793.
43. (e) Petragnani, N.; Comasseto, J. V. Synthesis 1991, 897.
44. (f) Tang, Y.; Ye, S.; Huang, Z.-Z.; Huang, Y.-Z. Heteroat. Chem. 2002, 13, 463.
45. Osuka, A.; Mori, Y.; Shimizu, H.; Suzuki, H. Tetrahedron Lett. 1983, 24, 2599.
46. Lieser, J. K. Synth. Commun. 1983, 13, 765.
47. 4.
48. (a) Tang, Y.; Huang, Y.-Z.; Dai, L.-X.; Chi, Z.-F.; Shi, L.-P. J. Org. Chem. 1996, 61, 5762.
49. (b) Ye, S.; Yuan, L.; Huang, Z.-Z.; Tang, Y.; Dai, L.-X. J. Org. Chem. 2000, 65, 6257.