Lewis acid-catalyzed allylic amination of allylsilanes and allylstannanes with [N-(p-toluenesulfonyl)imino]phenyliodinane

Bulletin of the Korean Chemical Society

Volumn 22, Issue 3, 2001, Pages 315-317

  Kim, Dae Young ^a   Kim, Hee Suk ^a   Park, Eun Ju ^a   Mang, Joo Yang ^a   Lee, Kilsung ^b  

^a Soonchunhyang University   (South Korea)

^b Cheil Industries Inc   (South Korea)

Author keywords

N (p Toluenesulfonyl)imino phenyliodinane; Allylicamines; Allylsilanes; Allylstannanes; Amination

Indexed keywords

[N (4 TOLUENESULFONYL)IMINO]PHENYLIODINANE; ALLYL COMPOUND; IMINE; PHOSPHONIC ACID DERIVATIVE; SILANE DERIVATIVE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ANALYTIC METHOD; CATALYSIS; CHEMICAL MODIFICATION; NOTE; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0342962080     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Note

References (33)

1. (a) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301.
2. (b) Bower, J. F.; Jumnah, R.; Willams, A. C.; Willams, J. M. J. J. Chem. Soc. Perkin Trans. 1 1997, 1411.
3. (c) Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron 1995, 51, 11087.
4. (d) Trost B. M.; van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444.
5. (a) Michalson, E. T.; Szmuszkovicz, J. Prog. Drug Res. 1989, 22, 135.
6. (b) Prashad, M. J. Med. Chem. 1993, 36, 631.
7. (c) Walsh, C. Tetrahedron 1982, 38, 871.
8. (d) Stutz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 320.
9. (a) Jain, P.; Garraffo, H. M.; Spande, T. F.; Yeh, H. J. C.; Daly, J. W. J. Nat. Prod. 1995, 58. 100.
10. (b) Reina, M. Merioli, A. H.; Cabrere, R.; Gonzales-Coloma, C. Phytochemistry 1995, 38, 355.
11. (c) Genisson, Y.; Mehmandoust, M.; Marazano, C.; Das, B. C. Hetrocycles 1994, 39, 811.
12. (d) Bergdahl, M.; Hett, R.; Griebe, T. L.; Gangloff, A. R.; Iqbal, J.; Wu, Y.; Helquist, P. Tetrahedron Lett. 1993, 34, 7371.
13. For a review on allylic amine synthesis, see: (a) Cheikh, R. B.; Chaabouni, R.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685.
14. (b) Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689.
15. (a) Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933.
16. (b) Cho, C. K.; Lim, Y. K.; Lee, K. S.; Jung, I. H.; Yoon, M. Y. Synth. Commun. 2000, 30, 1643.
17. (c) Cook, G. R.; Shanker, P. S. Tetrahedron Lett. 1998, 39, 4991.
18. (d) Pyne, S. G.; David, D. M.; Dong, Z. Tetrahedron Lett. 1998, 39, 8499.
19. (e) Lei, A.; Lu, X. Org. Lett. 2000, 2, 2357.
20. (f) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761.
21. (g) Evans, P. A.; Robinson, J. E. Org. Lett. 1999, 1, 1929.
22. (h) Takeuchi, R.; Shiga, N. Org. Lett. 1999, 1, 265.
23. (a) Takada, H.; Oda, M.; Miyake, Y.; Ohe, K.; Uemura, S. Chem. Commun. 1998, 1557.
24. (b) Albone, D. P.; Aujla, P. S.; Tayer, P. C.; Challenger, S.; Derrick, A. M. J. Org. Chem. 1998, 63, 9569.
25. (c) Srivastava, M.; Nicholas, K. M. J. Chem. Soc. Chem. Commun. 1998, 2705.
26. (d) Masse, C.; Knight, B. S.; Stavropoulos, P.; Panek, J. S. J. Am. Chem. Soc. 1997, 119, 6040.
27. Kim, D. Y.; Mang, J. Y.; Oh, D. Y. Synth. Commun. 1994, 24, 629.
28. Lee, K.; Kim, D. Y.; Oh, D. Y. Tetrahedron Lett. 1988, 29, 667.
29. Kim, D. Y.; Rhie, D. Y. Tetrahedron 1997, 53, 13603.
30. For the preliminary report of this work, see: Kim, D. Y.; Choi, J. S.; Rhie, D. Y.; Chang, S. K.; Kim, I. O. Synth. Commun. 1997, 27, 2753.
31. (a) Yamada, Y.; Yamamoto, T.; Okuwara, M. Chem. Lett. 1975, 361.
32. (b) Besenyei, G.; Nemeth, S.; Simandi, L. I. Tetrahedron Lett. 1993, 34, 6105.
33. Brandt, P.; Soderson, J.; Andersson, P. G.; Norrby, P.-O. J. Am. Chem. Soc. 2000, 122, 8013.