An unusual copper catalyzed iodine mediated aziridination of olefins with the direct use of p-toluenesulphonamide

Synthetic Communications

Volumn 35, Issue 1, 2005, Pages 9-13

  Jain, Suman L ^a   Sharma, Vishal B ^a   Sain, Bir ^a  

^a CSIR INDIAN INSTITUTE OF PETROLEUM   (India)

Author keywords

Aziridination; Copper; Iodine; Olefins; p toluenesulphonamide

Indexed keywords

3 METHYLSTYRENE; 4 CHLOROSTYRENE; 4 METHYLSTYRENE; ACETONITRILE; ALKENE; ALPHA METHYLSTYRENE; AZIRIDINE DERIVATIVE; COPPER; CYCLOHEPTENE; CYCLOHEXENE DERIVATIVE; IODINE; METHACRYLIC ACID METHYL ESTER; METHYLCINNAMATE; STYRENE; TOLUENESULFONAMIDE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLCYCLOHEXANE;

ARTICLE; AZIRIDINATION; CATALYST; CHEMICAL REACTION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE; THIN LAYER CHROMATOGRAPHY;

EID: 13944267818     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200046475     Document Type: Article

References (23)

1. Deyrup, J. A. The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; Wiley: New York, 1983; Vol. 42, pp. 1-214 part 1.
2. Padwa, A.; Woolhouse, A. D. Aziridines and fused ring derivatives. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, pp. 47-93.
3. Padwa, A.; Woolhouse, A. D. Comprehensive Heterocyclic Chemistry: The Structure Reactions and Synthesis and Uses of Heterocyclic Compounds; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, p. 47.
4. Kemp, J. E. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, p. 469.
5. Edwards, O. E. Acylnitrenes. In Nitrenes; Lwowski, W., Ed.; Interscience: New York, 1970; pp. 225-247.
6. Lwowski, W. Carbonylnitrenes. In Nitrenes; Lwowski, W., Ed.; Interscience: New York, 1970; pp. 185-224.
7. Lwowski, W. Acylazides and Nitrenes. In Azides and Nitrenes, Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: New York, 1984; pp. 205-246.
8. Yamada, Y.; Yamamoto, T.; Okawara, M. Synthesis and reaction of new type I-N Ylide, N-Tosyliminoiodinane. Chem Lett. 1975, 361.
9. Evans, D. A.; Faul, M. M.; Bilodeau, M. T. Copper catalyzed aziridination of olefins by N-(p-Toluenesulphonyl)imino phenyliodinane. J. Org. Chem. 1991, 56, 6744.
10. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Andersen, B. A.; Barnes, D. M. Bis(oxazoline)-copper complexes as chiral catalysts for enantioselective aziridination of olefins. J. Am. Chem. Soc. 1993, 115, 5328.
11. Li, Z.; Conser, K. R.; Jacobsen, E. N. Asymmetric alkene aziridination with readily available chiral diamine based catalysts. J. Am. Chem. Soc. 1993, 115, 5326.
12. Evans, D. A.; Faul, M. M.; Bilodeau, M. T. Development of the copper catalyzed olefin aziridination reaction. J. Am. Chem. Soc. 1994, 116, 2742.
13. Llewellyn, D. B.; Adamson, D.; Arndtsen, B. A. A novel example of chiral counter anion induced enantioselective metal catalysis: The importance of ion-pairing in copper-catalyzed olefin aziridination and cyclopropanation. Org. Lett. 2000, 2, 4165.
14. Simkhovich, L.; Gross, Z. Iron (IV) corrols are potent catalysts for aziridination of olefins by chloramine-T. Tetrahedron Lett. 2001, 42, 8089.
15. Ando, T.; Kano, D.; Minakata, S.; Ryu, I.; Komatsu, M. Iodine-catalyzed aziridination of alkenes using chloramine-T as a nitrogen source. Tetrahedron 1998, 54, 13485.
16. Ando, T.; Minakata, S.; Ryu, I.; Komatsu, M. Nitrogen atom transfer to alkenes utilizing chloramine-T as a nitrogen source. Tetrahedron Lett. 1998, 39, 309.
17. Vyas, R.; Chanda, B. M.; Bedekar, A. W. Bromamine-T: A superior source of nitrene for aziridination of olefins. Tetrahedron Lett. 1998, 39, 4715.
18. Albone, D. P.; Aujla, P. S.; Taylor, P. C.; Challenger, S.; Derrick, A. M. A simple copper catalyst for both aziridination of alkenes and amination of activated hydrocarbons with chloramine-T.Trihydrate. J. Org. Chem. 1998, 63, 9569.
19. Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. Bromine-catalyzed aziridination of olefins. A rare example of atom-transfer redox catalysis by a main group element. J. Am. Chem. Soc. 1998, 120, 6844.
20. Brandt, P.; Sodergren, M. J.; Anderson, P. O.; Norrby, P. O. Mechanistic studies of the copper catalyzed alkene aziridination. J. Am. Chem. Soc. 2000, 122, 8013.
21. Southwick, P. L.; Christman, D. R. Reactions of unsaturated compounds with iodine-amine complexes I. Reactions of benzlactophenone and benzalacetone. J. Am. Chem. Soc. 1952, 74, 1886.
22. Cromwell, N. H.; Mohrbacher, R. Ethylenimine ketones. X. The stereoisomerism of 1-Cyclohexyl-2-methyl-3-(p-phenylbenzyl)-ethylenimine. J. Am. Chem. Soc. 1953 75, 6252.
23. Cromwell, N. H.; Cahoy, R. P.; Franklin, W. E.; Mercer, G. D. Ethylamine ketones XI steric controls in the formation of the isomer ethylamine ketones. J. Am. Chem. Soc. 1957, 79, 922.