A new approach to hydrindenones by tautomer-arrested annulations of Fischer carbene complexes

Chemical Communications

Volumn , Issue 16, 1996, Pages 1863-1864

  Bos, Mary Ellen ^a   Wulff, William D ^a   Wilson, Kenneth J ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003131708     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960001863     Document Type: Article

References (21)

1. For synthetic applications of carbene complexes, see: K. H. Dötz, Angew. Chem., 1984, 23, 587; Angew. Chem., Int. Ed. Engl., 1984, 23, 587; W. D. Wulff, in Advances in Metal-Organic Chemistry, ed. L. S. Liebeskind, JAI Press, Greenwich, Connecticut, 1989, vol. 1; W. D. Wulff, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, 1990, vol. 5; W. D. Wulff, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; L. S. Hegedus, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; M. Doyle, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12.
2. For synthetic applications of carbene complexes, see: K. H. Dötz, Angew. Chem., 1984, 23, 587; Angew. Chem., Int. Ed. Engl., 1984, 23, 587; W. D. Wulff, in Advances in Metal-Organic Chemistry, ed. L. S. Liebeskind, JAI Press, Greenwich, Connecticut, 1989, vol. 1; W. D. Wulff, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, 1990, vol. 5; W. D. Wulff, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; L. S. Hegedus, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; M. Doyle, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12.
3. For synthetic applications of carbene complexes, see: K. H. Dötz, Angew. Chem., 1984, 23, 587; Angew. Chem., Int. Ed. Engl., 1984, 23, 587; W. D. Wulff, in Advances in Metal-Organic Chemistry, ed. L. S. Liebeskind, JAI Press, Greenwich, Connecticut, 1989, vol. 1; W. D. Wulff, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, 1990, vol. 5; W. D. Wulff, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; L. S. Hegedus, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; M. Doyle, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12.
4. For synthetic applications of carbene complexes, see: K. H. Dötz, Angew. Chem., 1984, 23, 587; Angew. Chem., Int. Ed. Engl., 1984, 23, 587; W. D. Wulff, in Advances in Metal-Organic Chemistry, ed. L. S. Liebeskind, JAI Press, Greenwich, Connecticut, 1989, vol. 1; W. D. Wulff, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, 1990, vol. 5; W. D. Wulff, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; L. S. Hegedus, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; M. Doyle, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12.
5. For synthetic applications of carbene complexes, see: K. H. Dötz, Angew. Chem., 1984, 23, 587; Angew. Chem., Int. Ed. Engl., 1984, 23, 587; W. D. Wulff, in Advances in Metal-Organic Chemistry, ed. L. S. Liebeskind, JAI Press, Greenwich, Connecticut, 1989, vol. 1; W. D. Wulff, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, 1990, vol. 5; W. D. Wulff, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; L. S. Hegedus, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; M. Doyle, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12.
6. For synthetic applications of carbene complexes, see: K. H. Dötz, Angew. Chem., 1984, 23, 587; Angew. Chem., Int. Ed. Engl., 1984, 23, 587; W. D. Wulff, in Advances in Metal-Organic Chemistry, ed. L. S. Liebeskind, JAI Press, Greenwich, Connecticut, 1989, vol. 1; W. D. Wulff, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, 1990, vol. 5; W. D. Wulff, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; L. S. Hegedus, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; M. Doyle, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12.
7. For synthetic applications of carbene complexes, see: K. H. Dötz, Angew. Chem., 1984, 23, 587; Angew. Chem., Int. Ed. Engl., 1984, 23, 587; W. D. Wulff, in Advances in Metal-Organic Chemistry, ed. L. S. Liebeskind, JAI Press, Greenwich, Connecticut, 1989, vol. 1; W. D. Wulff, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, 1990, vol. 5; W. D. Wulff, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; L. S. Hegedus, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12; M. Doyle, in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, 1995, vol. 12.
8. K. H. Dötz, J. Organomet. Chem., 1977, 140, 177; W. D. Wulff, K. S. Chan and P. C. Tang, J. Org. Chem., 1984, 49, 2293.
9. K. H. Dötz, J. Organomet. Chem., 1977, 140, 177; W. D. Wulff, K. S. Chan and P. C. Tang, J. Org. Chem., 1984, 49, 2293.
10. G. A. Peterson, F. A. Kunng, J. S. McCallum and W. D. Wulff, Tetrahedron Lett., 1987, 28, 1381.
11. (a) A. M. Gilbert and W. D. Wulff, J. Am. Chem. Soc., 1994, 116, 7449;
12. (b) R. L. Beddoes, J. D. King and P. Quayle, Tetrahedron Lett., 1995, 36, 3027;
13. (c) R. Neidlein, S. Gurtler and C. Krieger, Helv. Chim. Acta., 1994, 77, 2303.
14. For a recent list of applications to natural products synthesis, see ref. 1(c).
15. K. H. Dötz, R. E. Dietz, C. Kappenstein, D. Neugebauer and U. Schubert, Chem. Ber., 1979, 112, 3682. Only one other example (ref. 7) of this reaction has been reported (ref. 8, 9).
16. W. D. Wulff, P. C. Tang, K. S. Chan, J. S. McCallum, D. C. Yang and S. R. Gilbertson, Tetrahedron, 1985, 5813.
17. The reaction of the 2,6-difluorophenyl carbene complex analogous to 1 with diphenylacetylene give different products: K. H. Dötz and W. Sturm, J. Organomet. Chem., 1986, 310, C22.
18. The reaction of 1,3-dialkyl-2-indolyl carbene complexes give cyclohexadienone products: W. E. Bauta, W. D. Wulff, S. F. Pavkovic and E. J. Zaluzec, J. Org. Chem., 1989, 54, 3249.
19. Cyclohexadienones are known products from the reactions of β,β-disubstituted alkenyl carbene complexes (ref. 11) and with certain indolyl carbene complexes (ref. 9).
20. P. C. Tang and W. D. Wulff, J. Am. Chem. Soc., 1984, 106, 1132.
21. W. D. Wulff and D. C. Yang, J. Am. Chem. Soc., 1984, 106, 7565.