Novel catalytic and asymmetric process for aziridination mediated by sulfur ylides

Journal of Organic Chemistry

Volumn 61, Issue 24, 1996, Pages 8368-8369

  Aggarwal, Varinder K ^a   Thompson, Alison ^a   Jones, Ray V H ^b   Standen, Mike C H ^b  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001334291     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961754s     Document Type: Article

References (32)

1. (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
2. (b) For a review of methods in aziridination see: Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742-2753.
3. (a) Hansen, K. B.; Finney, N. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 676-678.
4. (b) Rasmussen, K. G.; Jorgensen, K. A. J. Chem. Soc., Chem. Commun. 1995, 1401-1402.
5. (c) Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60, 7090-7091.
6. (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328-5329.
7. (b) Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326-5327.
8. (c) Müller, P.; Baud, C.; Jacquier, Y. Tetrahedron 1996, 52, 1543-1548.
9. Vedejs, E.; Lin, S. J. Org. Chem. 1994, 59, 1602-1603.
10. (b) It has recently been shown that p-nitroaryl sulfonamides can be cleaved by addition of thiols; Fukuyama, T.; Jow, C. K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373-6374.
11. (a) Franzen, V.; Driesen, H. E. Chem. Ber. 1963, 96, 1881-1890.
12. (b) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353-1364.
13. (c) Tewari, R. S.; Awasthi, A. K.; Awasthi, A. Synthesis 1983, 330-331.
14. (d) Li, A. H.; Dai, L. X.; Hou, X. L. J. Chem. Soc., Chem. Commun. 1996, 491-492.
15. (e) Dai has recently reported the preparation of vinylic aziridines using catalytic amounts of sulfide under basic conditions; Li, A. H.; Dai, L. X.; Hou, X. L. J. Chem. Soc., Perkin Trans. 1 1996, 867-869.
16. Aggarwal, V. K.; Abdel-Rahman, H.; Jones, R. V. H.; Lee, H. Y.; Reid, B. D. J. Am. Chem. Soc. 1994, 116, 5973-5974.
17. Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004-7005.
18. Slow addition is required to limit the extent of dimerisation of the diazocompound: Doyle, M. P.; Griffin, J. H.; Bagheri, V.; Dorow, R. L. Organometallics 1984, 3, 53-61.
19. It has been shown that the nature of the group on nitrogen determines the efficiency of the addition of carbenoids to imines. Electron-donating groups result in high yields; electron-withdrawing groups result in low yields. See ref 2b. This issue would become important in the development of an asymmetric process.
20. Neither silyl nor phenyl groups on nitrogen are sufficiently electron withdrawing to activate the imine toward nucleophilic attack by the sulfur ylide.
21. 2: Osborn, H. M. I.; Sweeney, J. B. Synlett 1994, 145-147.
22. 2: Osborn, H. M. I.; Sweeney, J. B. Synlett 1994, 145-147.
23. Weinreb, S. M.; Demko, D. M.; Lessen, T. A. Tetrahedron Lett. 1986, 27, 2099-2102. The SES group has been shown to be easily removed from amines by fluoride.
24. From cross-over experiments, we have shown that these reactions are under kinetic control. Full details will be published elsewhere.
25. N,N-Diethyldiazoacetamide was prepared according to the method of Regitz for the preparation of tert-butyl diazoacetate. N,N-Diethylacetoacetamide was used in place of tert-butyl acetoacetate: Regitz, M.; Hocker, J.; Liedhegener, A. Organic Synthesis; Wiley: New York, 1973; Collect. Vol. V, pp 179-183. Rando, R. R. J. Am.Chem. Soc. 1972, 94, 1629-1631.
26. N,N-Diethyldiazoacetamide was prepared according to the method of Regitz for the preparation of tert-butyl diazoacetate. N,N-Diethylacetoacetamide was used in place of tert-butyl acetoacetate: Regitz, M.; Hocker, J.; Liedhegener, A. Organic Synthesis; Wiley: New York, 1973; Collect. Vol. V, pp 179-183. Rando, R. R. J. Am.Chem. Soc. 1972, 94, 1629-1631.
27. N,N-Diethyldiazoacetamide was prepared according to the method of Regitz for the preparation of tert-butyl diazoacetate. N,N-Diethylacetoacetamide was used in place of tert-butyl acetoacetate: Regitz, M.; Hocker, J.; Liedhegener, A. Organic Synthesis; Wiley: New York, 1973; Collect. Vol. V, pp 179-183. Rando, R. R. J. Am.Chem. Soc. 1972, 94, 1629-1631.
28. This is presumably because the 1,2 steric interaction on the three-membered ring between the SES group (this is the largest group) and either of the substituents is greater than the 1,2 steric interaction between the substituents themselves. It has also been found that, under equilibrating conditions, cis-unsaturated N-tosylaziridines were formed in preference to the Irons isomers: Mimura, N.; Ibuka, T.; Akaji, M.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 351-352.
29. In related epoxidation reactions (ref 7), Sulfide 1 was found to give high enantioselectivity in reactions with PhCHO (93% ee).
30. Aggarwal, V. K.; Abdel-Rahman, H.; Li, F.; Jones, R. V. H.; Standen, M. C. H. Chem. Bur. J. 1996, 2, 1024-1030.
31. 2 prepared by the method of Cervelló followed by sublimation was successful: Cervelló, J.; Marquet, J.; Moreno-Mañas, M. Synth. Commun. 1990, 20, 1931-1941.
32. D +311 (c 0.53 EtOH)). The absolute configuration of the N-SES-trans-2,3-diphenylaziridine could thus be deduced to be R,R.