Novel chemoselectivity and stereochemical aspects of nickel-catalyzed [2 + 2 + 2] cycloadditions

Journal of the American Chemical Society

Volumn 121, Issue 2, 1999, Pages 476-477

  Seo, Jeongbeob ^a   Chui, Helen M P ^a   Heeg, Mary Jane ^a   Montgomery, John ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NICKEL;

ARTICLE; CATALYSIS; CYCLIZATION; DIMERIZATION; POLYMERIZATION; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STEREOSPECIFICITY; X RAY ANALYSIS;

EID: 0033585539     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983081w     Document Type: Article

References (19)

1. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
2. Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539-644.
3. Montgomery, J.; Oblinger, E.; Savchenko, A. V. J. Am. Chem. Soc. 1997, 119, 4911-4920.
4. Montgomery, J.; Savchenko, A. V. J. Am. Chem. Soc. 1996, 118, 2099-2100.
5. For a recent exception, see: Ikeda, S.; Watanabe, H.; Sato, Y. J. Org. Chem. 1998, 63, 7026-7029.
6. Ikeda, S.; Mori, N.; Sato, Y. J. Am. Chem. Soc. 1997, 119, 4779-4780.
7. Montgomery, J.; Seo, J. Tetrahedron 1998, 54, 1131-1144.
8. Sato, Y.; Nishimata, T.; Mori, M. J. Org. Chem. 1994, 59, 6133-6135.
9. Chalk, A. J. J. Am. Chem. Soc. 1972, 94, 5928-5929.
10. Tsuda, T.; Kiyoi, T.; Miyane, T.; Saegusa, T. J. Am. Chem. Soc. 1988, 110, 8570-8572.
11. Lautens, M.; Edwards, L. G.; Tam, W.; Lough, A. J. J. Am. Chem. Soc. 1995, 117, 10276-10291.
12. The author has deposited atomic coordinates for 4 and 6 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
13. Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1987, 109, 4753-4755.
14. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962-2963.
15. Rigby, J. H.; Henshilwood, J. A. J. Am. Chem. Soc. 1991, 113, 5122-5123.
16. Treatment of α-methyl enone (E)-5 to the dimerization reaction conditions led to two major and three minor inseparable regioisomers of a different [2 + 2 + 2] cycloaddition product in which one enone and two alkynes were incorporated.
17. A mixed [2 + 2 + 2] cycloaddition reaction between the parent alkynyl enone (E)-1 and 2-methyl-1-phenylprop-2-en-1-one was attempted. However, a 90% isolated yield of the alkynyl enone dimer with no incorporation of the α-methylenone was obtained.
18. In addition to the products shown in eq 2. several isomers of the [2 + 2 + 2] product between 2 equiv of methyl vinyl ketone and the alkyne of (E)-5 were isolated.
19. Nickel enolates are known to be carbon bound. Treatment of a carbonbound nickel enolate with methyl vinyl ketone resulted only in acid/base exchange. Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30-44.