Reactions of Fischer carbene complexes with siloxydienes: Formation of cycloheptadiene and cyclopentene derivatives - Formal [2+1] cycloaddition followed by cope rearrangement versus formal [3+2] cycloaddition with or without preceding carbene-ligand metathesis

Chemistry - A European Journal

Volumn 5, Issue 3, 1999, Pages 876-882

  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; Metathesis; Rearrangements; Silicon

Indexed keywords

ALKADIENE; CYCLOPENTENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTRON; ELECTRONICS; MOLECULAR RECOGNITION; REACTION ANALYSIS; SYNTHESIS; THERMAL ANALYSIS;

EID: 0032989511     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990301)5:3<876::AID-CHEM876>3.0.CO;2-T     Document Type: Article

References (52)

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19. b) K. Takeda, Y. Okamoto, A. Nakajima, E. Yoshii, T. Koizumi, Synlett 1997, 1181-1183. For reactions of 2-amino-1,3-butadiene derivatives see: J. Barluenga, F. Aznar, A. Martin, J. T. Vázquez, J. Am. Chem. Soc. 1995, 117, 9419-9426; J. Barluenga, F. Aznar, M. Fernández, Chem. Eur. J. 1997, 3, 1629-1637, and references therein. For a [4+2] cycloaddition of α,β-unsaturated chromium-carbene complexes with Danishefsky's diene see: J. Barluenga, F. Aznar, S. Barluenga, S. Garcia-Granda, C. Alvarez-Rua, Synlett 1997, 1040-1042.
20. b) K. Takeda, Y. Okamoto, A. Nakajima, E. Yoshii, T. Koizumi, Synlett 1997, 1181-1183. For reactions of 2-amino-1,3-butadiene derivatives see: J. Barluenga, F. Aznar, A. Martin, J. T. Vázquez, J. Am. Chem. Soc. 1995, 117, 9419-9426; J. Barluenga, F. Aznar, M. Fernández, Chem. Eur. J. 1997, 3, 1629-1637, and references therein. For a [4+2] cycloaddition of α,β-unsaturated chromium-carbene complexes with Danishefsky's diene see: J. Barluenga, F. Aznar, S. Barluenga, S. Garcia-Granda, C. Alvarez-Rua, Synlett 1997, 1040-1042.
21. b) K. Takeda, Y. Okamoto, A. Nakajima, E. Yoshii, T. Koizumi, Synlett 1997, 1181-1183. For reactions of 2-amino-1,3-butadiene derivatives see: J. Barluenga, F. Aznar, A. Martin, J. T. Vázquez, J. Am. Chem. Soc. 1995, 117, 9419-9426; J. Barluenga, F. Aznar, M. Fernández, Chem. Eur. J. 1997, 3, 1629-1637, and references therein. For a [4+2] cycloaddition of α,β-unsaturated chromium-carbene complexes with Danishefsky's diene see: J. Barluenga, F. Aznar, S. Barluenga, S. Garcia-Granda, C. Alvarez-Rua, Synlett 1997, 1040-1042.
22. For a preliminary communication of selected reactions see: M. Hoffmann, M. Buchert, H.-U. Reißig, Angew. Chem. 1997, 109, 281-283; Angew. Chem. Int. Ed. Engl. 1997, 36, 283-285.
23. For a preliminary communication of selected reactions see: M. Hoffmann, M. Buchert, H.-U. Reißig, Angew. Chem. 1997, 109, 281-283; Angew. Chem. Int. Ed. Engl. 1997, 36, 283-285.
24. This isomerization may occur by (Lewis acid induced) methanol elimination and readdition.
25. For a related synthesis of cyclohepta-1,3-diones see: J. Barluenga, F. Aznar, C. Valdés, A. Martin, S. Garcia-Granda, E. Martin, J. Am. Chem. Soc. 1993, 115, 4403-4404; J. Barluenga, F. Aznar, A. Martin, S. Garcia-Granda, M. A. Salvado, P. Pertierra, J. Chem. Soc. Chem. Commun. 1993, 319-320.
26. For a related synthesis of cyclohepta-1,3-diones see: J. Barluenga, F. Aznar, C. Valdés, A. Martin, S. Garcia-Granda, E. Martin, J. Am. Chem. Soc. 1993, 115, 4403-4404; J. Barluenga, F. Aznar, A. Martin, S. Garcia-Granda, M. A. Salvado, P. Pertierra, J. Chem. Soc. Chem. Commun. 1993, 319-320.
27. For a related effect see: D. F. Harvey, K. P. Lund, J. Am. Chem. Soc. 1991, 113, 8916-8919 and ref. [3b].
28. See ref. [6a] and the discussion in ref. [5].
29. 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.
30. 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.
31. One of the referees suggested a stepwise formation of 25 by a Michael addition/cyclization sequence via a chairlike transition state for the first reaction. We cannot exclude this alternative, but a lower degree of stereoselectivity may arise when zwitterionic intermediates are involved.
32. 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 of the formation of isolable amino carbene complexes are given in: J. Barluenga, F. Aznar, A. Martin, Organometallics 1995, 14, 1429-1433. For a recent review including metathesis see: D. F. Harvey, D. M. Sigano, Chem. Rev. 1996, 96, 271-288.
33. 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 of the formation of isolable amino carbene complexes are given in: J. Barluenga, F. Aznar, A. Martin, Organometallics 1995, 14, 1429-1433. For a recent review including metathesis see: D. F. Harvey, D. M. Sigano, Chem. Rev. 1996, 96, 271-288.
34. 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 of the formation of isolable amino carbene complexes are given in: J. Barluenga, F. Aznar, A. Martin, Organometallics 1995, 14, 1429-1433. For a recent review including metathesis see: D. F. Harvey, D. M. Sigano, Chem. Rev. 1996, 96, 271-288.
35. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Engl. 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 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, vol. 5, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512 -1524; Angew. Chem. Int. Ed. Engl. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group; J. W. Herndon, Adv. Met. Org. Chem. 1994, 3, 51-95; A. de Meijere, Pure Appl. Chem. 1996, 68, 61-72; J. Barluenga, Pure Appl. Chem. 1996, 68, 543-552.
36. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Engl. 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 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, vol. 5, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512 -1524; Angew. Chem. Int. Ed. Engl. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group; J. W. Herndon, Adv. Met. Org. Chem. 1994, 3, 51-95; A. de Meijere, Pure Appl. Chem. 1996, 68, 61-72; J. Barluenga, Pure Appl. Chem. 1996, 68, 543-552.
37. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Engl. 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 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, vol. 5, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512 -1524; Angew. Chem. Int. Ed. Engl. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group; J. W. Herndon, Adv. Met. Org. Chem. 1994, 3, 51-95; A. de Meijere, Pure Appl. Chem. 1996, 68, 61-72; J. Barluenga, Pure Appl. Chem. 1996, 68, 543-552.
38. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Engl. 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 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, vol. 5, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512 -1524; Angew. Chem. Int. Ed. Engl. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group; J. W. Herndon, Adv. Met. Org. Chem. 1994, 3, 51-95; A. de Meijere, Pure Appl. Chem. 1996, 68, 61-72; J. Barluenga, Pure Appl. Chem. 1996, 68, 543-552.
39. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Engl. 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 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, vol. 5, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512 -1524; Angew. Chem. Int. Ed. Engl. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group; J. W. Herndon, Adv. Met. Org. Chem. 1994, 3, 51-95; A. de Meijere, Pure Appl. Chem. 1996, 68, 61-72; J. Barluenga, Pure Appl. Chem. 1996, 68, 543-552.
40. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Engl. 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 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, vol. 5, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512 -1524; Angew. Chem. Int. Ed. Engl. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group; J. W. Herndon, Adv. Met. Org. Chem. 1994, 3, 51-95; A. de Meijere, Pure Appl. Chem. 1996, 68, 61-72; J. Barluenga, Pure Appl. Chem. 1996, 68, 543-552.
41. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Engl. 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 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, vol. 5, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512 -1524; Angew. Chem. Int. Ed. Engl. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group; J. W. Herndon, Adv. Met. Org. Chem. 1994, 3, 51-95; A. de Meijere, Pure Appl. Chem. 1996, 68, 61-72; J. Barluenga, Pure Appl. Chem. 1996, 68, 543-552.
42. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Engl. 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 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, vol. 5, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512 -1524; Angew. Chem. Int. Ed. Engl. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group; J. W. Herndon, Adv. Met. Org. Chem. 1994, 3, 51-95; A. de Meijere, Pure Appl. Chem. 1996, 68, 61-72; J. Barluenga, Pure Appl. Chem. 1996, 68, 543-552.
43. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Engl. 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 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, vol. 5, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512 -1524; Angew. Chem. Int. Ed. Engl. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group; J. W. Herndon, Adv. Met. Org. Chem. 1994, 3, 51-95; A. de Meijere, Pure Appl. Chem. 1996, 68, 61-72; J. Barluenga, Pure Appl. Chem. 1996, 68, 543-552.
44. Review: K. H. Dötz, Angew. Chem. 1984, 96, 573-594; Angew. Chem. Int. Ed. Engl. 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 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, vol. 5, pp. 1065-1127; R. Aumann, Angew. Chem. 1988, 100, 1512 -1524; Angew. Chem. Int. Ed. Engl. 1988, 27, 1456; C. Betschart, L. S. Hegedus, J. Am. Chem. Soc. 1992, 114, 5010-5017, and earlier publications by this group; J. W. Herndon, Adv. Met. Org. Chem. 1994, 3, 51-95; A. de Meijere, Pure Appl. Chem. 1996, 68, 61-72; J. Barluenga, Pure Appl. Chem. 1996, 68, 543-552.
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48. This preparation is analogous to the procedure of Vedjes et al.: a) E. Vedjes, Z. H. Eberlein, D. J. Mazur, C. K. McClure, D. A. Perry, R. Ruggeri, E. Schwartz, J. Stults, D. J. Varie, R. G. Wilde, S. Wittenberger, J. Org. Chem. 1986, 51, 1556-1562.
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50. B. Frey, Dissertation, Technische Hochschule Darmstadt, 1992. Also see: J. Oren, M. Demuth, B. Fuchs, Synthesis 1987, 850-853.
51. B. Frey, Dissertation, Technische Hochschule Darmstadt, 1992. Also see: J. Oren, M. Demuth, B. Fuchs, Synthesis 1987, 850-853.
52. For metathesis reactions of complex 1 which generate this olefin see: E. O. Fischer, K. H. Dötz, Chem. Ber. 1972, 105, 3966-3973.