Rearrangement of Fischer carbene complexes to ketones: Stereochemistry and mechanism

Organometallics

Volumn 15, Issue 13, 1996, Pages 2881-2889

  Sathe, Kashinath M ^a,b   Nandi, Malay ^a,c   Amin, Sk Rasidul ^a   Puranik, Vedavati G ^a   Sarkar, Amitabha ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b Gauri Fine Chemicals   (India)

^c NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000950434     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960243t     Document Type: Article

References (60)

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4. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503. (e) Hegedus, L. S. Pure Appl. Chem. 1990, 62, 691. (f) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L, S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1. (g) Dötz, K. H. In Organometallics in Organic Synthesis: Aspects of a Modern Interdisplinary Field; tom Dieck, H., de Meijere, A., Eds.; Springer: Berlin, 1988. (h) Chan, K. S.; Peterson, G. A.; Brandvold, T. A.; Faron, K. L.; Challener, C. A.; Hyldahl, C.; Wulff, W. D. J. Organomet. Chem. 1987, 334, 9. (i) Wulff, W. D.; Tang, P. C.; Chan, K. S.; MeCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813. (j) Semmelhack, M. F.; Bozell, J. J.; Keller, L.; Sato, T.; Spiess, E. J.; Wulff, W.; Zask, A. Tetrahedron 1985, 41, 5803. (k) Casey, C. P. React. Intermed. 1985, 3. (l) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1984. (m) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689.
5. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503. (e) Hegedus, L. S. Pure Appl. Chem. 1990, 62, 691. (f) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L, S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1. (g) Dötz, K. H. In Organometallics in Organic Synthesis: Aspects of a Modern Interdisplinary Field; tom Dieck, H., de Meijere, A., Eds.; Springer: Berlin, 1988. (h) Chan, K. S.; Peterson, G. A.; Brandvold, T. A.; Faron, K. L.; Challener, C. A.; Hyldahl, C.; Wulff, W. D. J. Organomet. Chem. 1987, 334, 9. (i) Wulff, W. D.; Tang, P. C.; Chan, K. S.; MeCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813. (j) Semmelhack, M. F.; Bozell, J. J.; Keller, L.; Sato, T.; Spiess, E. J.; Wulff, W.; Zask, A. Tetrahedron 1985, 41, 5803. (k) Casey, C. P. React. Intermed. 1985, 3. (l) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1984. (m) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689.
6. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503. (e) Hegedus, L. S. Pure Appl. Chem. 1990, 62, 691. (f) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L, S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1. (g) Dötz, K. H. In Organometallics in Organic Synthesis: Aspects of a Modern Interdisplinary Field; tom Dieck, H., de Meijere, A., Eds.; Springer: Berlin, 1988. (h) Chan, K. S.; Peterson, G. A.; Brandvold, T. A.; Faron, K. L.; Challener, C. A.; Hyldahl, C.; Wulff, W. D. J. Organomet. Chem. 1987, 334, 9. (i) Wulff, W. D.; Tang, P. C.; Chan, K. S.; MeCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813. (j) Semmelhack, M. F.; Bozell, J. J.; Keller, L.; Sato, T.; Spiess, E. J.; Wulff, W.; Zask, A. Tetrahedron 1985, 41, 5803. (k) Casey, C. P. React. Intermed. 1985, 3. (l) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1984. (m) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689.
7. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503. (e) Hegedus, L. S. Pure Appl. Chem. 1990, 62, 691. (f) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L, S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1. (g) Dötz, K. H. In Organometallics in Organic Synthesis: Aspects of a Modern Interdisplinary Field; tom Dieck, H., de Meijere, A., Eds.; Springer: Berlin, 1988. (h) Chan, K. S.; Peterson, G. A.; Brandvold, T. A.; Faron, K. L.; Challener, C. A.; Hyldahl, C.; Wulff, W. D. J. Organomet. Chem. 1987, 334, 9. (i) Wulff, W. D.; Tang, P. C.; Chan, K. S.; MeCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813. (j) Semmelhack, M. F.; Bozell, J. J.; Keller, L.; Sato, T.; Spiess, E. J.; Wulff, W.; Zask, A. Tetrahedron 1985, 41, 5803. (k) Casey, C. P. React. Intermed. 1985, 3. (l) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1984. (m) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689.
8. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503. (e) Hegedus, L. S. Pure Appl. Chem. 1990, 62, 691. (f) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L, S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1. (g) Dötz, K. H. In Organometallics in Organic Synthesis: Aspects of a Modern Interdisplinary Field; tom Dieck, H., de Meijere, A., Eds.; Springer: Berlin, 1988. (h) Chan, K. S.; Peterson, G. A.; Brandvold, T. A.; Faron, K. L.; Challener, C. A.; Hyldahl, C.; Wulff, W. D. J. Organomet. Chem. 1987, 334, 9. (i) Wulff, W. D.; Tang, P. C.; Chan, K. S.; MeCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813. (j) Semmelhack, M. F.; Bozell, J. J.; Keller, L.; Sato, T.; Spiess, E. J.; Wulff, W.; Zask, A. Tetrahedron 1985, 41, 5803. (k) Casey, C. P. React. Intermed. 1985, 3. (l) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1984. (m) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689.
9. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503. (e) Hegedus, L. S. Pure Appl. Chem. 1990, 62, 691. (f) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L, S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1. (g) Dötz, K. H. In Organometallics in Organic Synthesis: Aspects of a Modern Interdisplinary Field; tom Dieck, H., de Meijere, A., Eds.; Springer: Berlin, 1988. (h) Chan, K. S.; Peterson, G. A.; Brandvold, T. A.; Faron, K. L.; Challener, C. A.; Hyldahl, C.; Wulff, W. D. J. Organomet. Chem. 1987, 334, 9. (i) Wulff, W. D.; Tang, P. C.; Chan, K. S.; MeCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813. (j) Semmelhack, M. F.; Bozell, J. J.; Keller, L.; Sato, T.; Spiess, E. J.; Wulff, W.; Zask, A. Tetrahedron 1985, 41, 5803. (k) Casey, C. P. React. Intermed. 1985, 3. (l) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1984. (m) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689.
10. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503. (e) Hegedus, L. S. Pure Appl. Chem. 1990, 62, 691. (f) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L, S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1. (g) Dötz, K. H. In Organometallics in Organic Synthesis: Aspects of a Modern Interdisplinary Field; tom Dieck, H., de Meijere, A., Eds.; Springer: Berlin, 1988. (h) Chan, K. S.; Peterson, G. A.; Brandvold, T. A.; Faron, K. L.; Challener, C. A.; Hyldahl, C.; Wulff, W. D. J. Organomet. Chem. 1987, 334, 9. (i) Wulff, W. D.; Tang, P. C.; Chan, K. S.; MeCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813. (j) Semmelhack, M. F.; Bozell, J. J.; Keller, L.; Sato, T.; Spiess, E. J.; Wulff, W.; Zask, A. Tetrahedron 1985, 41, 5803. (k) Casey, C. P. React. Intermed. 1985, 3. (l) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1984. (m) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689.
11. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503. (e) Hegedus, L. S. Pure Appl. Chem. 1990, 62, 691. (f) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L, S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1. (g) Dötz, K. H. In Organometallics in Organic Synthesis: Aspects of a Modern Interdisplinary Field; tom Dieck, H., de Meijere, A., Eds.; Springer: Berlin, 1988. (h) Chan, K. S.; Peterson, G. A.; Brandvold, T. A.; Faron, K. L.; Challener, C. A.; Hyldahl, C.; Wulff, W. D. J. Organomet. Chem. 1987, 334, 9. (i) Wulff, W. D.; Tang, P. C.; Chan, K. S.; MeCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813. (j) Semmelhack, M. F.; Bozell, J. J.; Keller, L.; Sato, T.; Spiess, E. J.; Wulff, W.; Zask, A. Tetrahedron 1985, 41, 5803. (k) Casey, C. P. React. Intermed. 1985, 3. (l) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1984. (m) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689.
12. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503. (e) Hegedus, L. S. Pure Appl. Chem. 1990, 62, 691. (f) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L, S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1. (g) Dötz, K. H. In Organometallics in Organic Synthesis: Aspects of a Modern Interdisplinary Field; tom Dieck, H., de Meijere, A., Eds.; Springer: Berlin, 1988. (h) Chan, K. S.; Peterson, G. A.; Brandvold, T. A.; Faron, K. L.; Challener, C. A.; Hyldahl, C.; Wulff, W. D. J. Organomet. Chem. 1987, 334, 9. (i) Wulff, W. D.; Tang, P. C.; Chan, K. S.; MeCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813. (j) Semmelhack, M. F.; Bozell, J. J.; Keller, L.; Sato, T.; Spiess, E. J.; Wulff, W.; Zask, A. Tetrahedron 1985, 41, 5803. (k) Casey, C. P. React. Intermed. 1985, 3. (l) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1984. (m) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689.
13. For reviews, see: (a) Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5. (b) Grotjahn, D. B.; Dötz, K. H. Synlett 1991, 381. (c) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (d) Rudler, H.; Audouin, M.; Chelain, E.; Denise, B.; Goumont, R.; Massoud, A.; Parlier, A.; Pacreau, A.; Rudler, M.; Yefsah, R.; Alvarez, C.; Delgado-Reyes, F. Chem. Soc. Rev. 1991, 20, 503. (e) Hegedus, L. S. Pure Appl. Chem. 1990, 62, 691. (f) Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L, S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1. (g) Dötz, K. H. In Organometallics in Organic Synthesis: Aspects of a Modern Interdisplinary Field; tom Dieck, H., de Meijere, A., Eds.; Springer: Berlin, 1988. (h) Chan, K. S.; Peterson, G. A.; Brandvold, T. A.; Faron, K. L.; Challener, C. A.; Hyldahl, C.; Wulff, W. D. J. Organomet. Chem. 1987, 334, 9. (i) Wulff, W. D.; Tang, P. C.; Chan, K. S.; MeCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813. (j) Semmelhack, M. F.; Bozell, J. J.; Keller, L.; Sato, T.; Spiess, E. J.; Wulff, W.; Zask, A. Tetrahedron 1985, 41, 5803. (k) Casey, C. P. React. Intermed. 1985, 3. (l) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissel, F. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, FL, 1984. (m) Dötz, K. H. Pure Appl. Chem. 1983, 55, 1689.
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57. 6 in the NMR probe at 50 °C. Only the peaks due to the starting material gradually disappeared and those of the product gained in intensity.
58. If the steric interaction between the benzylic and the ortho substituent alone determines the relative stereochemistry of the kinetic product, the role of the metal in deciding stereoselection cannot be crucial. Though this could suggest the intermediacy of an alternative structure other than II (Scheme 7) to produce the rearranged product, such a structure is not immediately apparent.
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