Direct use of allylic alcohols for platinum-catalyzed monoallylation of amines

Organic Letters

Volumn 9, Issue 17, 2007, Pages 3371-3374

  Utsunomiya, Masaru ^a   Miyamoto, Yoshiki ^a   Lpposhi, Junji ^a   Ohshima, Takashi ^a   Mashima, Kazushi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; ALLYL COMPOUND; AMINE; PLATINUM; PROPANOL;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ALLYL COMPOUNDS; AMINATION; AMINES; CATALYSIS; PLATINUM; PROPANOLS;

EID: 34548175723     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071365s     Document Type: Article

References (43)

1. For reviews, see: (a) Cheikh, R. B.; Chaabouni, R.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685.
2. (b) Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689.
3. (c) Trost, B. M.; Crawley, M. L.' Chem. Rev. 2003, 103, 2921.
4. For reviews, see: (a) Akutagawa, S.; Tani, K. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
5. (b) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; Wiley-VCH: New York, 1994; Chapter 3, p 95.
6. For reviews, see: (a) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vols 1-3.
7. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlar, D. Angew. Chem., int. Ed. 2005, 44, 4490.
8. For reviews, see: (a) Tsuji, J. Transition Metal Reagents and Catalysis; Wiley-VCH: Weinheim, Germany, 2000.
9. (b) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
10. Trost, B. M. Science 1991, 254, 1471.
11. For a review, see: Muzart, J. Eur. J. Org. Chem. 2007, 3077 and references cited therein.
12. Lumin, S.; Falck, J. R.; Capdevila, J.; Karara, A. Tetrahedron Lett. 1992, 33, 2091.
13. Lu, X.; Lu, L.; Sun, J. J. Mol. Catal 1987, 41, 245.
14. Lu, X.; Jiang, X.; Tao, X. J. Organomet. Chem. 1988, 344, 109.
15. Tsay, S.; Lin, L. C.; Furth, P. A.; Shum. C. C.; King, D. B.; Yu, S. F.; Chen, B.; Hwu, J. R. Synthesis 1993, 329.
16. (a) Kimura, M.; Tomizawa, T.; Horino, Y.; Tanaka, S.; Tamaru, Y. Tetrahedron Utt. 2000, 41, 3627.
17. (b) Kimura, M.; Horino, Y.; Mukai, R.; Tanaka, S.; Tamaru, Y. J. Am. Chem. Soc. 2001, 123, 10401.
18. (c) Kimura, M.; Futamata, M.; Shibata, K.; Tamaru, Y. Chem. Commun. 2003, 234.
19. Stary, I.; Stará, I. G.; Kocovsky, P. Tetrahedron Lett. 1993, 34, 179.
20. (a) Masuyama, Y.; Takahara, J, P.; Kurusu, Y. J. Am. Chem. Soc. 1988, 110, 4473.
21. (b) Masuyama. Y.; Kagawa, M.; Kurusu, Y. Chem. Lett. 1995, 1121.
22. (a) Itoh, K.; Hamaguchi, N.; Miura, M.; Nomura, M. J. Chem. Soc, Perkin Trans. I 1992, 2833.
23. (b) Satoh, T.; Ikeda, M.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4877.
24. (c) Yang, S.-C.; Hung, C-W. J. Org. Chem. 1999, 64, 5000.
25. (d) Yang, S.-C.; Tsai, Y.-C.; Shue, Y.-J. Organometallics 2001, 20, 5326.
26. (e) Shue, Y.-J.; Yang, S.-C.; Lai, H.-C. Tetrahedron Lett. 2003, 44, 1481.
27. Sakamoto, M.; Shimizu, I.; Yamamoto. A. Bull. Chem. Soc Jpn. 1996, 69, 1065.
28. Yamashita. Y.; Gopalarathnam, A.; Hartwig, J. F. J. Am. Chem. Soe ASAP.
29. (a) Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 10968.
30. (b) Ozawa, F.; Ishiyama, T.; Yamamoto, S.; Kawagishi, S.: Murakami, H.; Yoshifuji, M. Organometallics 2004, 23, 1698.
31. Kayaki, Y.; Koda, T.; Ikariya, T. J. Org. Chem. 2004, 69, 2595.
32. Kinoshita. H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 4085.
33. (a) Piechaczyk, O.; Doux, M.; Ricard, L.; Le Floch, P. Organometallics 2005, 24, 124.
34. (b) Piechaczyk, O.; Thoumazet, C.; Jean, Y.; Le Floch, P. J. Am. Chem. Soc. 2006, 128, 14306.
35. (c) Mora, G.; Deschamps, B.; van Zutphen, S.; Le, Goff, X. F.; Ricard, L.; Le Floch, P. Organometallics 2007, 26, 1846.
36. Guo, S.; Song, F.; Liu, Y. Synlett 2007, 964.
37. Very recently, efficient bismuth-catalyzed direct substitution of allylic alcohols with sulfonamides, carbamates, and carboxamides via carbenium intermediate was reported, see: Qin, H.; Yamagiwa, N.; Matsunaga, S.; Masakatsu, S. Angew. Chem., Int. Ed. 2007, 46, 409.
38. Pedley, J. B.; Marshall, E. M. J. Phys. Chem. Ref. Data 1983, 12, 967.
39. Due to the lack of information about bite angles of platinum complexes, those of palladium complexes are shown in Table 1.
40. See the Supporting Information for details.
41. Johns, A. M.; Utsunomiya, M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 1828.
42. Pt-catalyzed direct amination of allylic alcohols with ammonia to provide a mixture of mono-, di-, and triallylation products was reported, see: Ishimura, Y.; Nagato, N. Jpn. Kokai Tokkyo Koho JP 63002958, 1988.
43. Petranyi, G.; Ryder, N. S.; Stütz, A. Science 1984, 224, 1239.