Group 4 Metal Triflates as Efficient Catalysts for Allylations of Imines with Allyltributylstannane and Mannich-Type Reactions of Imines with Silyl Enol Ethers

Synlett

Volumn 1997, Issue 9, 1997, Pages 1099-1101

  Kobayashi, Shu ^a   Iwamoto, Shunsuke ^a   Nagayama, Satoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001903120     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1548     Document Type: Article

References (35)

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10. Quite recently, catalytic allylation reactions of imines promoted by a lanthanide triflate and a transition metal complex have been reported, (a) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. We have also found that lanthanide triflate-catalyzed allylation reactions proceed smoothly in acetonitrile as a solvent.
11. Quite recently, catalytic allylation reactions of imines promoted by a lanthanide triflate and a transition metal complex have been reported, (a) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. We have also found that lanthanide triflate-catalyzed allylation reactions proceed smoothly in acetonitrile as a solvent.
12. 3 are excellent catalysts for the activation of imines. For example, (a) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (b) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 5773. (c) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (d) Ishitani, H.; Nagayama, S.; Kobayashi, S. J. Org. Chem. 1996, 61, 1902. (e) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
13. 3 are excellent catalysts for the activation of imines. For example, (a) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (b) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 5773. (c) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (d) Ishitani, H.; Nagayama, S.; Kobayashi, S. J. Org. Chem. 1996, 61, 1902. (e) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
14. 3 are excellent catalysts for the activation of imines. For example, (a) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (b) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 5773. (c) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (d) Ishitani, H.; Nagayama, S.; Kobayashi, S. J. Org. Chem. 1996, 61, 1902. (e) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
15. 3 are excellent catalysts for the activation of imines. For example, (a) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (b) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 5773. (c) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (d) Ishitani, H.; Nagayama, S.; Kobayashi, S. J. Org. Chem. 1996, 61, 1902. (e) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
16. 3 are excellent catalysts for the activation of imines. For example, (a) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. (b) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 5773. (c) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195. (d) Ishitani, H.; Nagayama, S.; Kobayashi, S. J. Org. Chem. 1996, 61, 1902. (e) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
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21. As for catalysts in the reactions of imines with silyl enolates, (a) Guanti, G.; Narisano, E.; Banfi, L. Tetrahedron Lett. 1987, 28, 4331. (b) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (c) Mukaiyama, T.; Akamatsu, H. Han, J. S. Chem Lett. 1990, 889. (d) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (e) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721.
22. As for catalysts in the reactions of imines with silyl enolates, (a) Guanti, G.; Narisano, E.; Banfi, L. Tetrahedron Lett. 1987, 28, 4331. (b) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (c) Mukaiyama, T.; Akamatsu, H. Han, J. S. Chem Lett. 1990, 889. (d) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (e) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721.
23. As for catalysts in the reactions of imines with silyl enolates, (a) Guanti, G.; Narisano, E.; Banfi, L. Tetrahedron Lett. 1987, 28, 4331. (b) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (c) Mukaiyama, T.; Akamatsu, H. Han, J. S. Chem Lett. 1990, 889. (d) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (e) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721.
24. As for catalysts in the reactions of imines with silyl enolates, (a) Guanti, G.; Narisano, E.; Banfi, L. Tetrahedron Lett. 1987, 28, 4331. (b) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397. (c) Mukaiyama, T.; Akamatsu, H. Han, J. S. Chem Lett. 1990, 889. (d) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141. (e) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721.
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32. Review: (a) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (c) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
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34. (b) Kobayashi, S.; Moriwaki, M.; Akiyama, R.; Suzuki, S.; Hachiya, I. Tetrahedron Lett. 1996, 37, 7783.
35. (c) Kobayashi. S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977.