Study on Transmetalation of a Nickelacycle with Organometallic Reagents

Organometallics

Volumn 18, Issue 24, 1999, Pages 4891-4893

  Sato, Yoshihiro ^a   Takanashi, Tetsuya ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345831185     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990703t     Document Type: Article

References (23)

1. For reviews of transition-metal-catalyzed cycloadditions, see: (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
2. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
3. (a) For [4 + 4] cycloadditions, see: Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089 and references therein.
4. (b) For [4 + 2] cycloadditions, see: Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255 and references therein.
5. (c) For a cyclization of 1,3-diene and allene, see: Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843.
6. (d) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. Tamao, K.; Kobayashi, K.; Ito, Y. J. Synth. Org. Chem. Jpn. 1990, 48, 381.
7. (d) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. Tamao, K.; Kobayashi, K.; Ito, Y. J. Synth. Org. Chem. Jpn. 1990, 48, 381.
8. (e) For a cyclization of 1,3-diene and a tethered α,β-unsaturated carbonyl group, see: Montgomery, J.; Oblinger, E.; Savchenko, A. V. J. Am. Chem. Soc. 1997, 119, 4911.
9. (a) Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771.
10. (b) Sato, Y.; Takimoto, M.; Mori, M. Tetrahedron Lett. 1996, 37, 887.
11. (c) Sato, Y.; Takimoto, M.; Mori, M. Synlett 1997, 734.
12. (d) Sato, Y.; Saito, N.; Mori, M. Tetrahedron Lett. 1997, 38, 3931.
13. (e) Sato, Y.; Saito, N.; Mori, M. Tetrahedron 1998, 54, 1153.
14. Sato, Y.; Takanashi, T.; Hoshiba, M.; Mori, M. Tetrahedron Lett. 1998, 39, 5579.
15. The transmetalation of oxanickelacycles and organometallic reagents has recently been reported by Montgomery in the Ni(0)-catalyzed cyclization of alkyne and tethered aldehyde and by Tamaru in the Ni(0)-catalyzed coupling of 1,3-dienes and aldehydes; see: (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 6098.
16. The transmetalation of oxanickelacycles and organometallic reagents has recently been reported by Montgomery in the Ni(0)- catalyzed cyclization of alkyne and tethered aldehyde and by Tamaru in the Ni(0)-catalyzed coupling of 1,3-dienes and aldehydes; see: (a) Oblinger, E.; Montgomery, J. J. Am. Chem. Soc. 1997, 119, 9065. Tang, X.-Q.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 6098.
17. (b) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397.
18. The stereochemistry of 9a and 13a was determined by NOE experiments.
19. The geometry of the olefin in 9b, 10b, 11, 12, and 13b was assigned to be E on the basis of the NOE experiments.
20. One of the reviews pointed out the possibility that the nickel complex 4a or 4b in Scheme 2 would remain associated with the alkoxide to form a nickelate species and the reductive elimination would derive from the nickelate intermediate. This possibility cannot be ruled out by our present results.
21. Kroll, W. R.; Naegele, W. J. Organomet. Chem. 1969, 19, 439.
22. In the case of DIBAL-H (run 5), it is possible that the intermediate 14a (R = H) instead of 14-i-Bu was formed by transmetalation of 7 using hydride on the Al atom. It was thought that 14a (R = H) would show almost the same reactivity as that of 15a, producing 13a in preference to 13b.
23. 2Zn (Table 1, run 4).