New Surprises with Fischer Carbene Complexes: Formal [3 + 2] Cycloadditions with and without Preceding Carbene-Ligand Metathesis

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 3, 1997, Pages 283-285

  Hoffmann, Matthias ^a   Buchert, Matthias ^b   Reissig, Hans Ulrich ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Carbene complexes; Chromium; Cycloadditions; Dienes; Metathesis

Indexed keywords

EID: 0030945984     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199702831     Document Type: Article

References (29)

1. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Eng. 1984, 23, 587; H.-U. Reissig in Organic Synthesis Highlights (Eds.: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig), VCH, Weinheim 1991, pp. 186-191; W. D. Wulff in Comprehensive Organic Synthesis Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512-1524; Angew. Chem. Int. Ed. Eng. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group.
2. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Eng. 1984, 23, 587; H.-U. Reissig in Organic Synthesis Highlights (Eds.: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig), VCH, Weinheim 1991, pp. 186-191; W. D. Wulff in Comprehensive Organic Synthesis Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512-1524; Angew. Chem. Int. Ed. Eng. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group.
3. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Eng. 1984, 23, 587; H.-U. Reissig in Organic Synthesis Highlights (Eds.: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig), VCH, Weinheim 1991, pp. 186-191; W. D. Wulff in Comprehensive Organic Synthesis Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512-1524; Angew. Chem. Int. Ed. Eng. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group.
4. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Eng. 1984, 23, 587; H.-U. Reissig in Organic Synthesis Highlights (Eds.: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig), VCH, Weinheim 1991, pp. 186-191; W. D. Wulff in Comprehensive Organic Synthesis Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512-1524; Angew. Chem. Int. Ed. Eng. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group.
5. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Eng. 1984, 23, 587; H.-U. Reissig in Organic Synthesis Highlights (Eds.: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig), VCH, Weinheim 1991, pp. 186-191; W. D. Wulff in Comprehensive Organic Synthesis Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512-1524; Angew. Chem. Int. Ed. Eng. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group.
6. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Eng. 1984, 23, 587; H.-U. Reissig in Organic Synthesis Highlights (Eds.: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig), VCH, Weinheim 1991, pp. 186-191; W. D. Wulff in Comprehensive Organic Synthesis Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512-1524; Angew. Chem. Int. Ed. Eng. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group.
7. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Eng. 1984, 23, 587; H.-U. Reissig in Organic Synthesis Highlights (Eds.: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig), VCH, Weinheim 1991, pp. 186-191; W. D. Wulff in Comprehensive Organic Synthesis Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512-1524; Angew. Chem. Int. Ed. Eng. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group.
8. For the regioselective cyclopropanation of electron-poor 1,3-dienes with Fischer carbene complexes see: M. Buchert, M. Hoffmann, H.-U. Reissig, Chem. Ber. 1995, 128, 605-614. In this paper, further publications concerning the reaction of Fischer carbene complexes with different 1,3-dienes are compiled.
9. First examples: W. D. Wulff, D. C. Yang, C. K. Murray, J. Am. Chem. Soc. 1988, 110, 2653-2655. More recently, the investigations of Barluenga and co-workers are of importance: J. Barluenga, F. Aznar, A. Martin, J. T. Vázquez, J. Am. Chem. Soc. 1995, 117, 9419-9426, and references therein.
10. First examples: W. D. Wulff, D. C. Yang, C. K. Murray, J. Am. Chem. Soc. 1988, 110, 2653-2655. More recently, the investigations of Barluenga and co-workers are of importance: J. Barluenga, F. Aznar, A. Martin, J. T. Vázquez, J. Am. Chem. Soc. 1995, 117, 9419-9426, and references therein.
11. For syntheses and Diels-Alder reactions of the corresponding trimethylsiloxy-substituted diene see: J. Oren, M. Demuth, B. Fuchs, Synthesis 1987, 850-853.
12. 3): δ = 157.3 (s; C-3), 146.3, 137.2 (2 s; ipso-C-Ph), 134.0, 128.8 (2 d; HC=CH), 128.7, 127.2, 126.7 (3 d; Ph), 108.3 (d; C-2), 84.7 (s; C-4), 48.5 (t; C-5), 44.0 (d; C-1), 25.6 (2 q; tBu), 18.4, 18.1 (2 s; tBu), -3.0, -4.3, -4.6 (3 q; Me). The assignments were confirmed by 2D-and 1D-INADEQUATE experiments.
13. For competition between cyclopropanation and olefin metathesis see: C. P. Casey, N. L. Hornung, W. P. Kosar, J. Am. Chem. Soc. 1987, 109, 4908-4916 and references therein. More recent examples for the formation of isolable amino carbene complexes are given in: J. Barluenga, F. Aznar, A. Martin, Organometallics 1995, 14, 1429-1433.
14. For competition between cyclopropanation and olefin metathesis see: C. P. Casey, N. L. Hornung, W. P. Kosar, J. Am. Chem. Soc. 1987, 109, 4908-4916 and references therein. More recent examples for the formation of isolable amino carbene complexes are given in: J. Barluenga, F. Aznar, A. Martin, Organometallics 1995, 14, 1429-1433.
15. R. Aumann, H. Heinen, Chem. Ber. 1987, 120, 537-540.
16. M. Hoffmann, H.-U. Reissig, unpublished results; see also ref. [3] (Wulff et al.).
17. M. Hoffmann, H.-U. Reissig, Synlett 1995, 625-627. See ref. [14] therein for [3 + 2] cycloadditions of Fischer carbene complexes to alkynes; more recent work: B. L. Flynn, F. J. Funke, C. C. Silveira, A. de Meijere, Synlett 1995, 1007-1010. For [3 + 2] cycloadditions of alkyne carbene complexes to enamines, see: A. G. Meyer, R. Aumann, Synlett 1995, 1011-1013. For rhodium complex catalyzed [3 + 2] cycloadditions of vinyldiazo compounds to enol ethers see: H. M. L. Davies, B. Hu, E. Saikali, P. R. Bruzinski, J. Org. Chem. 1994, 59, 4535-4541.
18. M. Hoffmann, H.-U. Reissig, Synlett 1995, 625-627. See ref. [14] therein for [3 + 2] cycloadditions of Fischer carbene complexes to alkynes; more recent work: B. L. Flynn, F. J. Funke, C. C. Silveira, A. de Meijere, Synlett 1995, 1007-1010. For [3 + 2] cycloadditions of alkyne carbene complexes to enamines, see: A. G. Meyer, R. Aumann, Synlett 1995, 1011-1013. For rhodium complex catalyzed [3 + 2] cycloadditions of vinyldiazo compounds to enol ethers see: H. M. L. Davies, B. Hu, E. Saikali, P. R. Bruzinski, J. Org. Chem. 1994, 59, 4535-4541.
19. M. Hoffmann, H.-U. Reissig, Synlett 1995, 625-627. See ref. [14] therein for [3 + 2] cycloadditions of Fischer carbene complexes to alkynes; more recent work: B. L. Flynn, F. J. Funke, C. C. Silveira, A. de Meijere, Synlett 1995, 1007-1010. For [3 + 2] cycloadditions of alkyne carbene complexes to enamines, see: A. G. Meyer, R. Aumann, Synlett 1995, 1011-1013. For rhodium complex catalyzed [3 + 2] cycloadditions of vinyldiazo compounds to enol ethers see: H. M. L. Davies, B. Hu, E. Saikali, P. R. Bruzinski, J. Org. Chem. 1994, 59, 4535-4541.
20. M. Hoffmann, H.-U. Reissig, Synlett 1995, 625-627. See ref. [14] therein for [3 + 2] cycloadditions of Fischer carbene complexes to alkynes; more recent work: B. L. Flynn, F. J. Funke, C. C. Silveira, A. de Meijere, Synlett 1995, 1007-1010. For [3 + 2] cycloadditions of alkyne carbene complexes to enamines, see: A. G. Meyer, R. Aumann, Synlett 1995, 1011-1013. For rhodium complex catalyzed [3 + 2] cycloadditions of vinyldiazo compounds to enol ethers see: H. M. L. Davies, B. Hu, E. Saikali, P. R. Bruzinski, J. Org. Chem. 1994, 59, 4535-4541.
21. 3-complex and reductive elimination was postulated.
22. For considerations of α,β-unsaturated carbene complexes as chromabutadiene derivatives see: R. Aumann, P. Hinterding, Chem. Ber. 1990, 123, 2047-2051; R. Aumann, H. Heinen, P. Hinterding, N. Sträter, B. Krebs, ibid. 1991, 124, 1229-1236.
23. For considerations of α,β-unsaturated carbene complexes as chromabutadiene derivatives see: R. Aumann, P. Hinterding, Chem. Ber. 1990, 123, 2047-2051; R. Aumann, H. Heinen, P. Hinterding, N. Sträter, B. Krebs, ibid. 1991, 124, 1229-1236.
24. As for all Diels-Alder reactions of two 1,3-dienes, an exchange of diene and dienophile in our example also leads to identical products if the [4 + 2] cycloaddition is followed by a [3,3] sigmatropic rearrangement. We see no reason to discuss this more complicated alternative for our case.
25. Postulated Diels-Alder reactions of metalladienes: with palladium: B. M. Trost, A. S. K. Hashmi, J. Am. Chem. Soc. 1994, 116, 2183-2184; with rhodium: J. Schnaubelt, E. Marks, H.-U. Reissig, Chem. Ber. 1996, 129, 73-75.
26. Postulated Diels-Alder reactions of metalladienes: with palladium: B. M. Trost, A. S. K. Hashmi, J. Am. Chem. Soc. 1994, 116, 2183-2184; with rhodium: J. Schnaubelt, E. Marks, H.-U. Reissig, Chem. Ber. 1996, 129, 73-75.
27. L. A. Paquette, Top. Curr. Chem. 1984, 119, 1-158; T. Hudlicky, J. D. Price, Chem. Rev. 1989, 89, 1467-1486; for synthesis of cyclopentenes by formal [3 + 2] cycloaddition see: S. Ejiri, S. Yamago, E. Nakamura, J. Am. Chem. Soc. 1992, 114, 8707-8708, and references therein.
28. L. A. Paquette, Top. Curr. Chem. 1984, 119, 1-158; T. Hudlicky, J. D. Price, Chem. Rev. 1989, 89, 1467-1486; for synthesis of cyclopentenes by formal [3 + 2] cycloaddition see: S. Ejiri, S. Yamago, E. Nakamura, J. Am. Chem. Soc. 1992, 114, 8707-8708, and references therein.
29. L. A. Paquette, Top. Curr. Chem. 1984, 119, 1-158; T. Hudlicky, J. D. Price, Chem. Rev. 1989, 89, 1467-1486; for synthesis of cyclopentenes by formal [3 + 2] cycloaddition see: S. Ejiri, S. Yamago, E. Nakamura, J. Am. Chem. Soc. 1992, 114, 8707-8708, and references therein.