A facile highly regio- and stereoselective preparation of N-tosyl allylic amines from allylic alcohols and tosyl isocyanate via palladium(II)-catalyzed aminopalladation-β-heteroatom elimination

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2357-2360

  Lei, Aiwen ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000776614     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006130u     Document Type: Article

References (59)

1. (a) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689.
2. (b) Cheikh, R. B.; Chaabouni, R.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685.
3. (c) Wei, Z.-Y.; Knaus, E. E. Synthesis 1994, 1463.
4. (d) Spaltenstein, A.; Carpino, P. A.; Miyake, F.; Hopkins, P. B. J. Org. Chem. 1987, 52, 3759.
5. (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173.
6. (b) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelbach, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, p 585.
7. (c) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; John Wiley: Chichester, 1995.
8. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545.
9. (a) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730.
10. (b) Pretot, R.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 323.
11. (c) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Chem. Soc., Chem. Commun. 1997, 561.
12. (d) Hayashi, T.; Kishi, K.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1990, 31, 1743.
13. (e) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681.
14. (f) Trost, B. M.; Krische, M. J.; Radinov, R.; Zanoni, G. J. Am. Chem. Soc. 1996, 118, 6297.
15. (a) Tetsuo, T.; Horii, Y.; Nakagawa, Y.; Ishida, T.; Saegusa, T. J. Org. Chem. 1989, 54, 977.
16. (b) Tanikaga, R.; Takeuchi, J.; Takyu, M.; Kaji, A. J. Chem. Soc., Chem. Commun. 1987, 386.
17. (c) Genêt, J. P.; Balabane, M.; Bäckvall, J. E.; Nyström, J. E. Tetrahedron Lett. 1983, 27, 2745.
18. (d) Tsuji, J.; Ueno, H.; Kobayashi, Y.; Okumoto, H. Tetrahedron Lett. 1981, 22, 2573.
19. (e) Inami, H.; Ito, T.; Urabe, H.; Sato, F. Tetrahedron Lett. 1993, 34, 5919.
20. (f) Urade, H.; Inami, H.; Sato, F. J. Chem. Soc., Chem. Commun. 1993, 1595.
21. (g) Tsuji, J.; Yuhara, M.; Minato, M.; Yamada, H.; Sato, F.; Kobayashi, Y. Tetrahedron Lett. 1988, 29, 343.
22. (h) Hirao, T.; Enda, J.; Ohshiro, Y.; Agawa, T. Tetrahedron Lett. 1981, 22, 3079.
23. (i) Trost, B. M.; Self, C. R. J. Am. Chem. Soc. 1983, 105, 5942.
24. (j) Kang, J.; Cho, W.; Lee, W. K. J. Org. Chem. 1984, 49, 1838.
25. (a) Lu, X.; Zhu, G.; Wang, Z. Synlett 1998, 115.
26. (b) Lu, X.; Ma, S. New Age of Divalent Palladium Catalysis. In Transition Metal Catalyzed Reaction; Murahashi, S-I., Davies, S. G., Eds.; 1999; Chapter 6, p 133.
27. (c) Ma, S.; Lu, X. J. Chem. Soc., Chem. Commun. 1990, 733.
28. (d) Ma, S.; Lu, X. J. Org. Chem. 1991, 56, 5112.
29. (e) Ma, S.; Zhu, G.; Lu, X. J. Org. Chem. 1993, 58, 3692.
30. (f) Ma, S.; Lu. X. J. Organomet. Chem. 1993, 447, 305.
31. (g) Ma, S.; Lu, X. J. Org. Chem. 1993, 58, 1245.
32. (h) Zhu, G.; Ma, S.; Lu, X. J. Chem. Res. (S) 1993, 367.
33. (i) Zhu, G.; Lu, X.; Organometallics 1995, 14, 4899.
34. (j) Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087.
35. (a) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009.
36. (b) Ozawa, F.; Kabo, A.; Hayashi, T. Chem. Lett. 1992, 2177.
37. (c) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421.
38. A typical experiment showed that the products contained 37% of 3b, 51% of (E)-3e, and other unidentified products as characterized by HPLC.
39. Tamaru, Y.; Kimura, M.; Tanaka, S.; Kure, S.; Yoshida, Z. Bull. Chem. Soc. Jpn. 1994, 67, 2838.
40. Using the (E)-allylic alcohol as the substrate, no expected product formed.
41. 13
42. Wang, Z.; Zhang, Z.; Lu, X. Organometallics 2000, 19, 775.
43. (a) Markies, B. A.; Canty, A. J.; de Graaf, W.; Boersma, J.; Janssen, M. D.; Hogerheide, M. P.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Organomet. Chem. 1994, 482, 191.
44. (b) Ryabov, A. D.; Sakodinskaya, I.-K.; Titov, V. M.; Yatsimirsky, A. K. Inorg. Chim. Acta 1981, 54, L195.
45. (c) Ryabov, A. D.; Sakodinskaya, I.-K.; Yatsimirsky, A. K. Inorg. Chim. Acta 1986, 116, L55.
46. (a) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579.
47. (b) Henry, P. M. J. Am. Chem. Soc. 1972, 94, 5200.
48. (a) Overman, L. E.; Donde, Y. J. Am. Chem. Soc. 1999, 121, 2933.
49. (b) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449.
50. (c) Overman, L. E. Acc. Chem. Res. 1980, 13, 218.
51. (d) Genda, J.; Heiland, A. C.; Ernst, B. E.; Bellus, D. Synthesis 1993, 729.
52. (e) Tamaru, Y.; Kagotani, M.; Yoshida, Z.-I. J. Org. Chem. 1980, 45, 5221.
53. (f) Tamaru, Y.; Kagotani, M.; Yoshida, Z. Tetrahedron Lett. 1981, 22, 4245.
54. (g) Tamaru, Y.; Kagotani, M.; Yoshida, Z. J. Org. Chem. 1985, 50, 764.
55. (h) Schenck, T. G.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2058.
56. (i) Mehmandoust, M.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1992, 33, 4313.
57. (j) Mizutani, M.; Sanemitsu, Y.; Tamrau, Y.; Yoshida, Z.-I. J. Org. Chem. 1985, 50, 764.
58. (a) Wyle, M. J.; Fowler, F. W. J. Org. Chem. 1984, 49, 4025.
59. (b) Birtwistle, D. H.; Brown, J. M.; Foxton, M. W. Tetrahedron 1988, 44, 7309.