Reaction of azetidines with chloroformates

Organic Letters

Volumn 8, Issue 24, 2006, Pages 5501-5504

  Vargas Sanchez, Monica ^a   Lakhdar, Sami ^a   Couty, François ^a   Evano, Gwilherm ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845983275     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062128c     Document Type: Article

References (42)

1. Hageman, H. A. Org. React. 1953, 7, 198.
2. (a) Kapnang, H.; Charles, G. Tetrahedron Lett. 1983, 24, 3233.
3. (b) Cooley, J. H., Evain, E. J. Synthesis 1989, 1.
4. Ethyl chloroformate: (a) Flynn, E. H.; Murphy, H. W.; McMahon, R. E. J. Am. Chem. Soc. 1955, 77, 3104.
5. (b) Campbell, J. A. J. Org. Chem. 1957, 22, 1259.
6. Aryl chloroformates: (c) Hobson, J. D.; McCluskey, J. G. J. Chem. Soc. C 1967, 2015.
7. (d) Pfaffli, P.; Hauth, H. Helv. Chim. Acta 1973, 56, 347.
8. Vinylchloroformate: (e) Olofson, R. A.; Rodney, C. Schnur, R. C.; Bunes, L.; Pepe, J. P. Tetrahedron Lett. 1977, 18, 1567.
9. Chloroethyl chloroformate: (f) Olofson, R. A.; Martz, J. T.; Senet, J.-P.; Piteau, M.; Malfroot, T. J. Org. Chem. 1984, 49, 2081.
10. 2,2,2-Trichloroethyl chloroformate: (g) Montzka, T. A.; Matiskella, J. D.; Partyka, R. A. Tetrahedron Lett. 1974, 15, 1325.
11. β-Trimethylsilylethyl chloroformate: (h) Campbell, A. L.; Pilipauskas, D. R.; Khanna, I. K.; Rhodes, R. A. Tetrahedron Lett. 1987, 28, 2331.
12. Propargyl chloroformate: (i) Bhat, R. G.; Ghosh, Y.; Chandrasekaran, S. Tetrahedron Lett. 2004, 45, 7983.
13. (a) Sim, T. B.; Kang, S. H.; Lee, K. S.; Lee, W. K.; Ha, H.-J. J. Org. Chem. 2003, 68, 104.
14. (b) Park, C. H.; Kim, M. S.; Sim, T. B.; Pyun, D. K.; Lee, C. H.; Choi, D.; Lee, W. K.; Chang, J.-W.; Ha, H.-J. J. Org. Chem. 2003, 68, 43.
15. (c) Kim, Y.; Ha, H.-J.; Yun, H.; Lee, B. K.; Lee, W. K. Tetrahedron 2006, 62, 8844.
16. Ennis, D. S.; Ince, J.; Rahman, S.; Shipman, M. J. Chem. Soc., Perkin Trans. 1 2000, 2047.
17. Nitta, Y.; Yamaguchi, Y.; Tanaka, T. Heterocycles 1986, 24, 25.
18. (a) Vuilhorgne, M.; Commercon, A.; Mignani, S. Chem. Lett. 1999, 605.
19. (b) Tonder, J. E.; Hansen, J. B.; Begtrup, M.; Petterson, I.; Rimvall, K.; Christensen, B.; Ehrbar, U.; Olesen, P. H. J. Med. Chem. 1999, 42, 4970.
20. (a) Baumann, H.; Duthaler, R. O. Helv. Chim. Acta 1988, 71, 1035.
21. (b) Barrett, A. G. M.; Dozzo, P.; White, A. J. P.; Williams, D. J. Tetrahedron 2002, 58, 7303.
22. (a) Couty, F.; Evano, G.; Prim, D. Mini-Rev. Org. Chem. 2004, 1, 133.
23. (b) Couty, F.; Evano, G.; Vargas-Sanchez, M.; Bouzas, G. J. Org. Chem. 2005, 70, 9028.
24. (c) Vargas-Sanchez, M.; Couty, F.; Evano, G.; Prim, D.; Marrot, J. Org. Lett. 2005, 6, 5861.
25. (d) Bräuner-Osborne, H.; Bunch, L. Chopin, N., Couty, F.; Evano, G.; Jensen, A. A.; Kusk, M.; Nielsen, B.; Rabasso, N. Org. Biomol. Chem. 2005, 3926-3936.
26. (e) Sivaprakasam, M.; Couty, F.; Evano, G.; Srinivas, B.; Sridhar, R.; Rama Rao, K. Synlett 2006, 781.
27. (f) Couty, F.; David, O.; Durrat, F.; Evano, G.; Lakhdar, S.; Marrot, J.; Vargas-Sanchez, M. Eur. J. Org. Chem. 2006, 3479.
28. (a) 2-Cyano-azetidines: Agami, C.; Couty, F.; Evano, G. Tetrahedron: Asymmetry 2002, 13, 297.
29. (b) 2-Acyl-azetidines: Couty, F. Prim, D. Tetrahedron: Asymmetry 2002, 13, 2619.
30. (c) 2-Carboxy-azetidines: Couty, F.; Durrat, F.; Prim, D. Tetrahedron Lett. 2003, 44, 5209.
31. Also see ref 9b. (d) 2-Phosphinoyl-azetidines: Rabasso, N. Ph.D. dissertation. Université Pierre et Marie Curie, France, 2003.
32. Kim, Y.; Ha, H. J.; Han, K.; Ko, S. W.; Yun, H.; Yoon, H. J.; Kim, M. S.; Lee, W. K. Tetrahedron Lett. 2005, 46, 4407.
33. Reactions were in most cases too sluggish and did not go to completion with this particular all-cis azetidine when run in DCM. Therefore, they were all run in refluxing acetonitrile to have comparable results.
34. For a theoretical approach of the formation of oxazolidinones from aziridines, see: Testa, L.; Akssira, M.; Zaballos-García, E.; Arroyo, P.; Domingo, L. R.; Sepúlveda-Arques, J. Tetrahedron 2003, 59, 677.
35. (a) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
36. (b) Ziegler, T. Chem. Rev. 1991, 91, 651.
37. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
38. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
39. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986.
40. N2 reaction is known to proceed via a molecular complex. See for examples (a) Parthiban, S.; de Oliveira, G.; Martin, J. M. L. J. Phys. Chem. A 2001, 105, 895;
41. (b) Bouyacoub, A.; Jean, Y.; Volatron, F. J. Mol. Struct. 1996, 377, 51 and references cited therein.
42. Bach, R. D.; Dmitrenko, O. J. Org. Chem. 2002, 67, 3884.