Advances in nitrogen transfer reactions involving aziridines

Accounts of Chemical Research

Volumn 39, Issue 3, 2006, Pages 194-206

  Watson, Iain D G ^a   Yu, Lily ^a   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33645512284     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar050038m     Document Type: Article

References (47)

1. Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, Germany, 2006.
2. (a) Watson, I. D. G.; Yudin, A. K. New insights into the mechanism of palladium-catalyzed allylic amination. J. Am. Chem. Soc. 2005, 127, 17516-17529.
3. (b) Siu, T.; Picard, C. J.; Yudin, A. K. Development of electrochemical processes for nitrene generation and transfer. J. Org. Chem. 2005, 70, 932-937.
4. (c) Dalili, S.; Yudin, A. K. Transition metal catalyzed synthesis and reactivity of N-alkenyl aziridines. Org. Lett. 2005, 7, 1161-1164.
5. (d) Watson, I. D. G.; Styler, S. A.; Yudin, A. K. Unusual selectivity of unprotected aziridines in palladium-catalyzed allylic amination enables facile preparation of branched aziridines. J. Am. Chem. Soc. 2004, 126, 5086-5087.
6. (e) Sasaki, M.; Yudin, A. K. One-pot reduction-aldol reaction of esters. Synlett 2004, 2443-2444.
7. (f) Krasnova, L. B.; Hili, R. M.; Chernoloz, O. V.; Yudin, A. K. Phenyliodine(III) diacetate as a mild oxidant for aziridination of olefins and imination of sulfoxides with N-aminophthalimide. ARKIVOC 2004, 2005, 26-38.
8. (g) Dalili, S.; Caiazzo, A.; Yudin, A. K. Aziridine-derived iminophosphine ligands in palladium-catalyzed allylic substitution. J. Organomet. Chem. 2004, 689, 3604-3611.
9. (h) Watson, I. D. G.; Yudin, A. K. Ring-opening reactions of nonactivated aziridines catalyzed by tris(pentafluorophenyl)borane. J. Org. Chem. 2003, 68, 5160-5167.
10. (i) Sasaki, M.; Yudin, A. K. Oxidative cycloamination of olefins with aziridines as a versatile route to saturated nitrogen-containing heterocycles. J. Am. Chem. Soc. 2003, 125, 14242-14243.
11. (j) Sasaki, M.; Dalili, S.; Yudin, A. K. N-Arylation of aziridines. J. Org. Chem. 2003, 68, 2045-2047.
12. (k) Caiazzo, A.; Dalili, S.; Yudin, A. K. Lewis acid-catalyzed dimerization of N-unprotected aziridines. Synlett 2003, 2198-2202.
13. (l) Watson, I. D. G.; Yudin, A. K. Selective functionalization of small organic molecules using electrophilic nitrogen sources. Curr. Opin. Drug Discovery Dev. 2002, 5, 906-917.
14. (m) Caiazzo, A.; Dalili, S.; Yudin, A. K. Design and development of cyclohexane-based P,N-ligands for transition metal catalysis. Org. Lett. 2002, 4, 2597-2600.
15. (n) Siu, T.; Yudin, A. K. Practical olefin aziridination with a broad substrate scope. J. Am. Chem. Soc. 2002, 124, 530-531.
16. (o) Siu, T.; Yudin, A. K. Electrochemical imination of sulfoxides using N-aminophthalimide. Org. Lett. 2002, 4, 1839-1842.
17. (a) Stamm, H. Nucleophilic ring opening of aziridines. J. Prakt. Chem., Chem. Ztg. 1999, 341, 319-331.
18. (b) Hu, X. E. Nucleophilic ring opening of aziridines. Tetrahedron 2004, 60, 2701-2743.
19. (a) Li, Z.; Conser, K. R.; Jacobsen, E. N. Asymmetric alkene aziridination with readily available chiral diimine-based catalysts. J. Am. Chem. Soc. 1993, 115, 5326-5327.
20. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. Development of the copper-catalyzed olefin aziridination reaction. J. Am. Chem. Soc. 1994, 116, 2742-2753.
21. (c) Müller, P.; Baud, C.; Jacquier, Y. A method for rhodium(II)-catalyzed aziridination of olefins. Tetrahedron 1996, 52, 1543-1548.
22. (a) Carpino, L. A.; Kirkley, R. K. Stereochemistry of the oxidation of the cis- and trans-1-amino-2,3-diphenylaziridines. J. Am. Chem. Soc. 1970, 92, 1784-1786.
23. (b) Hoesch, L.; Dreiding, A. S. Phthalimidonitrene. I. Lead tetraacetate oxidation of N-aminophthalimide in inert solvents. Formation and properties of trans-1,4pdiphthaloyl-2-tetrazene. Helv. Chim. Acta 1975, 58, 980-1001.
24. (c) Atkinson, R. S.; Grimshire, M. J.; Kelly, B. J. Aziridination by oxidative addition of N-aminoquinazolones to alkenes: Evidence for non-involvement of N-nitrenes. Tetrahedron 1989, 45, 2875-2886.
25. (d) Atkinson, R. S.; Tughan, G. Asymmetric induction in addition of N-nitrenes to alkenes. Oxidation of 3-amino-2-(1,2,2-trimethylpropyl)quinazolin- 4(3H)-one in the presence of α-methylene-γ-butyrolactone: conformation analysis of the aziridines formed and comparison with alkanoylated cyclopropylamines. J. Chem. Soc., Perkin Trans. 1 1987, 12, 2797-2802.
26. (e) Atkinson, R. S.; Malpass, J. R.; Skinner, K. L.; Woodthorpe, K. L. Intramolecular reactions of N-nitrenes with alkenes. J. Chem. Soc., Perkin Trans. 1 1984, 8, 1905-1912.
27. (a) Siu, T.; Li, W.; Yudin, A. K. Parallel electrosynthesis of 1,2-diamines. J. Comb. Chem. 2001, 3, 554-558.
28. (b) Siu, T.; Li, W.; Yudin, A. K. Parallel electrosynthesis of α-alkoxycarbamates α-alkoxyamides, and α-alkoxysulfonamides using the spatially addressable electrolysis platform (SAEP). J. Comb. Chem. 2000, 2, 545-549.
29. (c) Siu, T.; Yekta, S.; Yudin, A. K. New approach to rapid generation and screening of diverse catalytic materials on electrode surfaces. J. Am. Chem. Soc. 2000, 122, 11787-11790.
30. Li, J.; Liang, J. L.; Chan, P. W. H.; Che, C. M. Aziridination of alkenes with N-substituted hydrazines mediated by iodobenzene diacetate. Tetrahedron Lett. 2004, 45, 2685-2688.
31. Wehn, P. M.; Lee, J.; Du Bois, J. Stereochemical models for Rh-catalyzed amination reactions of chiral sulfamates. Org. Lett. 2003, 5, 4823-4826.
32. Ham, G. E. Activated aziridines. I. Reaction of anilines with O-ethyl-N,N-ethyleneurethane. Mechanism & Hammett ρ-constant. J. Org. Chem. 1964, 29, 3052-3055.
33. Watson, I. D. G.; Yudin, A. K. University of Toronto, Toronto, Canada, unpublished results, 2003.
34. Sasaki, M.; Yudin, A. K. University of Toronto, Toronto, Canada, unpublished results, 2003.
35. Kodama, H.; Taiji, T.; Ohta, T.; Furukawa, I. Asymmetric allylic amination catalyzed by Pd-BINAP complexes. Synlett 2001, 385-387.
36. Our attempts to perform allylic amination reactions of NH aziridines with Rh and Ir catalysts have been unsuccessful. Watson, I. D. G.; Alphonse, F.-A.; Yudin, A. K. University of Toronto, Toronto, Canada, unpublished results, 2005.
37. (a) You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. Highly regio- and enantioselective Pd-catalyzed allylic alkylation and amination of monosubstituted allylic acetates with novel ferrocene P,N-ligands. J. Am. Chem. Soc. 2001, 123, 7471-7472.
38. (b) Hayashi, T.; Kishi, K.; Yamamoto, A.; Ito, Y. Asymmetric allylic amination catalyzed by chiral ferrocenylphosphine palladium complexes. Tetrahedron Lett. 1990, 31, 1743-1746.
39. (c) Faller, J. W.; Wilt, J. C. Palladium/BINAP(S)-catalyzed asymmetric allylic amination. Org. Lett. 2005, 7, 633-636.
40. 2 oxidation of functionalized acyclic alkenes versus alkene ionization potentials, HOMOs, and LUMOs. J. Am. Chem. Soc. 2001, 123, 1564-1568.
41. Lin, B. L.; Clough, C. R.; Hillhouse, G. L. Interactions of aziridines with nickel complexes: oxidative-addition and reductive-elimination reactions that break and make C-N bonds. J. Am. Chem. Soc. 2002, 124, 2890-2891.
42. Calet, S.; Urso, F.; Alper, H. Enantiospecific and stereospecific rhodium(I)-catalyzed carbonylation and ring expansion of aziridines. Asymmetric synthesis of β-actams and the kinetic resolution of aziridines. J. Am. Chem. Soc. 1989, 111, 931-934.
43. Tanner, D. Chiral aziridines: their synthesis and use in stereoselective transformations. Angew. Chem., Int. Ed. 1994, 33, 599-619.
44. (a) Dewick, P. M. Alkaloids. In Medicinal Natural Products: A Biosynthetic Approach, 2nd ed.; John Wiley & Sons Ltd: Chichester, England, 2002; Chapter 6.
45. (b) O'Hagan, D. Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids. Nat. Prod. Rep. 2000, 17, 435-446.
46. (a) Mitchinson, A.; Nadin, A. Saturated nitrogen heterocycles. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892.
47. (b) Pichon, M.; Figadère, B. Synthesis of 2,5-disubstituted pyrrolidines. Tetrahedron: Asymmetry 1996, 7, 927-964.