Competition between insertion and conjugate addition in nickel-catalyzed couplings of enones with unsaturated functional groups

Tetrahedron Letters

Volumn 37, Issue 38, 1996, Pages 6839-6842

  Montgomery, John ^a   Seo, Jeongbeob ^a   Chui, Helen M P ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE DERIVATIVE; CYCLOHEXANONE DERIVATIVE; KETONE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

GADUS MORHUA;

EID: 0030590452     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01528-6     Document Type: Article

References (22)

1. 1. (a) Montgomery, J.; Savchenko, A. V. J. Am. Chem. Soc. 1996, 118, 2099.
2. (b) Savchenko, A. V.; Montgomery, J. J. Org. Chem. 1996, 61, 1562.
3. 2. For a discussion of the effect of ring size on the rates of migratory insertions involving alkynes, see: Samsel, E. G.; Norton, J. R. J. Am. Chem. Soc. 1984, 106, 5505.
4. 3. For related processes involving carbometallation / conjugate addition sequences, see: a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841.
5. b) Lipshutz, B. H.; Dimock, S. H. J. Org. Chem. 1991, 56, 5761.
6. c) Ireland, R. E.; Wipf, P. J. Org. Chem. 1990, 55, 1425.
7. d) Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
8. 4. (a) Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015.
9. (b) Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975.
10. 5. (a) Lipshutz, B. H.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 7440.
11. (b) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1993, 115, 12625.
12. (c) Lipshutz, B. H.; Wood, M. R. J. Am. Chem. Soc. 1994, 116, 11689.
13. 6. (a) Loots, M. J.; Schwartz, J. J. Am. Chem. Soc. 1977, 99, 8046.
14. (b) Schwartz, J.; Loots, M. J., Kosugi, H. J. Am. Chem. Soc. 1980, 102, 1333.
15. 7. Babiak, K. A.; Behling, J. R.; Dygos, J. H.; McLaughlin, K. T.; Ng, J. S.; Kalish, V. J.; Kramer, S. W.; Shone, R. L., J. Am. Chem. Soc. 1990, 112, 7441.
16. 2ZrHCl is faster than alkyne hydrozirconation. (a) Lipschutz, B. H.; Bhandari, A.; Lindsley, C.; Keil, R.; Wood, M. R. Pure Appl. Chem. 1994, 66, 1493.
17. (b) Buchwald, S. L.; LaMaire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895.
18. 9. Montgomery, J.; Savchenko, A. V.; Zhao, Y. J. Org. Chem. 1995, 60, 5699.
19. 10. For related tandem Michael additions using other classes of nucleophiles, see: (a) Klimko, P. G.; Singleton, D. A. Synthesis 1994, 979.
20. (b) Shida, N.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1992, 57, 5049.
21. (c) Saito, S.; Hirohara, Y. Narahara, O. Moriwake T. J. Am. Chem. Soc. 1989, 111, 4533.
22. (d) Yoshii, E.; Hori, K.; Nomura, K.; Yamaguchi, K. Synlett 1995, 568 and references therein.