Unprecedented highly chemoselective allylation of imines in the presence of aldehydes via a palladium catalysed allylstannane reaction

Chemical Communications

Volumn , Issue 12, 1996, Pages 1459-1460

  Nakamura, Hiroyuki ^a   Iwama, Hideki ^a   Yamamoto, Yoshinori ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002061843     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960001459     Document Type: Article

References (7)

1. Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207, and references cited therein.
2. H. Nakamura, N. Asao and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1995, 1273.
3. Tsuji et al., reported a bis-π-allylpalladium intermediate, generated by palladium catalysed dimerization of butadiene, which reacted with aldehydes; K. Ohno, T. Mitsuya and J. Tsuji, Tetrahedron., 1972, 28, 3705 and references cited therein.
4. M. A. Ciufolini and G. O. Spencer, J. Org. Chem., 1989, 54, 4739; For transition metal catalysed addition of pronucleophiles to the imines, see Y. Yamamoto, Y. Kubota, Y. Honda, H. Fukui, N. Asao and H. Nemoto, J. Am. Chem. Soc., 1994, 116, 3161.
5. M. A. Ciufolini and G. O. Spencer, J. Org. Chem., 1989, 54, 4739; For transition metal catalysed addition of pronucleophiles to the imines, see Y. Yamamoto, Y. Kubota, Y. Honda, H. Fukui, N. Asao and H. Nemoto, J. Am. Chem. Soc., 1994, 116, 3161.
6. Principles and Applications of Organotransition Metal Chemistry, ed. J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, University Science Books, Mill Valley, 1987, pp. 57-66.
7. 1 Quite recently, catalytic allylation of imines promoted by lanthanide triflates has been reported; C. Bellucci, P. Cozzi and A. Umani-Ronchi, Tetrahedron Lett., 1995, 36, 7289. However, the chemical yields (30-70%) were generally low in the catalytic system.