1,4-Asymmetric induction in the formation of cyclohexadienones by chirality transfer from a transiently installed chromium-stereospecific electrocyclic ring closure of a metal complexed vinyl ketene

Chemical Communications

Volumn , Issue 6, 1997, Pages 615-616

  Hsung, Richard P ^a   Quinn, John F ^a   Weisenberg, Brian A ^a   Wulff, William D ^a   Yap, Glenn P A ^b   Rheingold, Arnold L ^b  

^a UNIVERSITY OF CHICAGO   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003617097     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a604742d     Document Type: Article

References (25)

1. R. P. Hsung; W. D. Wulff and A. L. Rheingold, J. Am. Chem. Soc., 1994, 116, 6449.
2. For subsequent examples, see: R. Neidlein, S. Gürtler and C. Krieger, Helv. Chim. Acta., 1994, 77, 2303; R. L. Beddoes, J. D. King and P. Quayle, 1995, 36, 3027; K. H. Dotz, C. Stinner and M. Nieger, J. Chem. Soc., Chem. Commun., 1995, 2535; R. P. Hsung, W. D. Wulff and C. A. Challener, Synthesis, 1996, 773.
3. For subsequent examples, see: R. Neidlein, S. Gürtler and C. Krieger, Helv. Chim. Acta., 1994, 77, 2303; R. L. Beddoes, J. D. King and P. Quayle, 1995, 36, 3027; K. H. Dotz, C. Stinner and M. Nieger, J. Chem. Soc., Chem. Commun., 1995, 2535; R. P. Hsung, W. D. Wulff and C. A. Challener, Synthesis, 1996, 773.
4. For subsequent examples, see: R. Neidlein, S. Gürtler and C. Krieger, Helv. Chim. Acta., 1994, 77, 2303; R. L. Beddoes, J. D. King and P. Quayle, 1995, 36, 3027; K. H. Dotz, C. Stinner and M. Nieger, J. Chem. Soc., Chem. Commun., 1995, 2535; R. P. Hsung, W. D. Wulff and C. A. Challener, Synthesis, 1996, 773.
5. For subsequent examples, see: R. Neidlein, S. Gürtler and C. Krieger, Helv. Chim. Acta., 1994, 77, 2303; R. L. Beddoes, J. D. King and P. Quayle, 1995, 36, 3027; K. H. Dotz, C. Stinner and M. Nieger, J. Chem. Soc., Chem. Commun., 1995, 2535; R. P. Hsung, W. D. Wulff and C. A. Challener, Synthesis, 1996, 773.
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7. W. D. Wulff, K. S. Chan and P. C. Tang, J. Org. Chem., 1984, 49, 2293; The corresponding cis-propenyl tungsten complex does not isomerize as rapidly: W. D. Wulff, W. E. Bauta, R. W. Kaesler, P. J. Lankford, R. A. Miller, C. K. Murray and D. C. Yang, J. Am. Chem. Soc., 1990, 112, 3642.
8. W. D. Wulff, K. S. Chan and P. C. Tang, J. Org. Chem., 1984, 49, 2293; The corresponding cis-propenyl tungsten complex does not isomerize as rapidly: W. D. Wulff, W. E. Bauta, R. W. Kaesler, P. J. Lankford, R. A. Miller, C. K. Murray and D. C. Yang, J. Am. Chem. Soc., 1990, 112, 3642.
9. For reviews on the synthetic applications of Fischer carbene complexes, see: W. D. Wulff, 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.
10. For reviews on the synthetic applications of Fischer carbene complexes, see: W. D. Wulff, 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.
11. For reviews on the synthetic applications of Fischer carbene complexes, see: W. D. Wulff, 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.
12. For discussions of, and recent citations to mechanistic issues, see (a) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell and J. Clardy, Organometallics, 1994, 13, 102; (b) J. Christoffers and K. H. Dötz, Chem. Ber., 1995, 128, 157; (c) J. W. Herndon and A. Hayford, Organometallics, 1995, 14, 1556; (d) M. F. Gross and M. G. Finn, J. Am. Chem. Soc., 1994, 116, 10921; (e) J. Barluenga, F. Aznar, A. Martin, S. Garcia-Granda and E. Perez-Carreno, J. Am. Chem. Soc., 1994, 116, 11191; (f) D. F. Harvey, E. M. Grenzer and P. K. Gantzel, J. Am. Chem. Soc., 1994, 116, 6719; (g) M. Duetsch, S. Vidoni, F. Stein, F. Funke, M. Noltemeyer and A. de Meijere, J. Chem. Soc., Chem. Commun., 1994, 1679; (h) C. Bouancheau, A. Parlier, M. Rudler, H. Rudler, J. Vaissermann and J.-C. Daran, Organometallics, 1994, 13, 4708; (i) J. R. Knorr and T. L. Brown, Organometallics, 1994, 13, 2178; (j) W. D. Wulff, A. M. Gilbert, R. P. Hsung and A. Rahm, J. Org. Chem., 1995, 60, 4566.
13. For discussions of, and recent citations to mechanistic issues, see (a) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell and J. Clardy, Organometallics, 1994, 13, 102; (b) J. Christoffers and K. H. Dötz, Chem. Ber., 1995, 128, 157; (c) J. W. Herndon and A. Hayford, Organometallics, 1995, 14, 1556; (d) M. F. Gross and M. G. Finn, J. Am. Chem. Soc., 1994, 116, 10921; (e) J. Barluenga, F. Aznar, A. Martin, S. Garcia-Granda and E. Perez-Carreno, J. Am. Chem. Soc., 1994, 116, 11191; (f) D. F. Harvey, E. M. Grenzer and P. K. Gantzel, J. Am. Chem. Soc., 1994, 116, 6719; (g) M. Duetsch, S. Vidoni, F. Stein, F. Funke, M. Noltemeyer and A. de Meijere, J. Chem. Soc., Chem. Commun., 1994, 1679; (h) C. Bouancheau, A. Parlier, M. Rudler, H. Rudler, J. Vaissermann and J.-C. Daran, Organometallics, 1994, 13, 4708; (i) J. R. Knorr and T. L. Brown, Organometallics, 1994, 13, 2178; (j) W. D. Wulff, A. M. Gilbert, R. P. Hsung and A. Rahm, J. Org. Chem., 1995, 60, 4566.
14. For discussions of, and recent citations to mechanistic issues, see (a) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell and J. Clardy, Organometallics, 1994, 13, 102; (b) J. Christoffers and K. H. Dötz, Chem. Ber., 1995, 128, 157; (c) J. W. Herndon and A. Hayford, Organometallics, 1995, 14, 1556; (d) M. F. Gross and M. G. Finn, J. Am. Chem. Soc., 1994, 116, 10921; (e) J. Barluenga, F. Aznar, A. Martin, S. Garcia-Granda and E. Perez-Carreno, J. Am. Chem. Soc., 1994, 116, 11191; (f) D. F. Harvey, E. M. Grenzer and P. K. Gantzel, J. Am. Chem. Soc., 1994, 116, 6719; (g) M. Duetsch, S. Vidoni, F. Stein, F. Funke, M. Noltemeyer and A. de Meijere, J. Chem. Soc., Chem. Commun., 1994, 1679; (h) C. Bouancheau, A. Parlier, M. Rudler, H. Rudler, J. Vaissermann and J.-C. Daran, Organometallics, 1994, 13, 4708; (i) J. R. Knorr and T. L. Brown, Organometallics, 1994, 13, 2178; (j) W. D. Wulff, A. M. Gilbert, R. P. Hsung and A. Rahm, J. Org. Chem., 1995, 60, 4566.
15. For discussions of, and recent citations to mechanistic issues, see (a) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell and J. Clardy, Organometallics, 1994, 13, 102; (b) J. Christoffers and K. H. Dötz, Chem. Ber., 1995, 128, 157; (c) J. W. Herndon and A. Hayford, Organometallics, 1995, 14, 1556; (d) M. F. Gross and M. G. Finn, J. Am. Chem. Soc., 1994, 116, 10921; (e) J. Barluenga, F. Aznar, A. Martin, S. Garcia-Granda and E. Perez-Carreno, J. Am. Chem. Soc., 1994, 116, 11191; (f) D. F. Harvey, E. M. Grenzer and P. K. Gantzel, J. Am. Chem. Soc., 1994, 116, 6719; (g) M. Duetsch, S. Vidoni, F. Stein, F. Funke, M. Noltemeyer and A. de Meijere, J. Chem. Soc., Chem. Commun., 1994, 1679; (h) C. Bouancheau, A. Parlier, M. Rudler, H. Rudler, J. Vaissermann and J.-C. Daran, Organometallics, 1994, 13, 4708; (i) J. R. Knorr and T. L. Brown, Organometallics, 1994, 13, 2178; (j) W. D. Wulff, A. M. Gilbert, R. P. Hsung and A. Rahm, J. Org. Chem., 1995, 60, 4566.
16. For discussions of, and recent citations to mechanistic issues, see (a) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell and J. Clardy, Organometallics, 1994, 13, 102; (b) J. Christoffers and K. H. Dötz, Chem. Ber., 1995, 128, 157; (c) J. W. Herndon and A. Hayford, Organometallics, 1995, 14, 1556; (d) M. F. Gross and M. G. Finn, J. Am. Chem. Soc., 1994, 116, 10921; (e) J. Barluenga, F. Aznar, A. Martin, S. Garcia-Granda and E. Perez-Carreno, J. Am. Chem. Soc., 1994, 116, 11191; (f) D. F. Harvey, E. M. Grenzer and P. K. Gantzel, J. Am. Chem. Soc., 1994, 116, 6719; (g) M. Duetsch, S. Vidoni, F. Stein, F. Funke, M. Noltemeyer and A. de Meijere, J. Chem. Soc., Chem. Commun., 1994, 1679; (h) C. Bouancheau, A. Parlier, M. Rudler, H. Rudler, J. Vaissermann and J.-C. Daran, Organometallics, 1994, 13, 4708; (i) J. R. Knorr and T. L. Brown, Organometallics, 1994, 13, 2178; (j) W. D. Wulff, A. M. Gilbert, R. P. Hsung and A. Rahm, J. Org. Chem., 1995, 60, 4566.
17. For discussions of, and recent citations to mechanistic issues, see (a) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell and J. Clardy, Organometallics, 1994, 13, 102; (b) J. Christoffers and K. H. Dötz, Chem. Ber., 1995, 128, 157; (c) J. W. Herndon and A. Hayford, Organometallics, 1995, 14, 1556; (d) M. F. Gross and M. G. Finn, J. Am. Chem. Soc., 1994, 116, 10921; (e) J. Barluenga, F. Aznar, A. Martin, S. Garcia-Granda and E. Perez-Carreno, J. Am. Chem. Soc., 1994, 116, 11191; (f) D. F. Harvey, E. M. Grenzer and P. K. Gantzel, J. Am. Chem. Soc., 1994, 116, 6719; (g) M. Duetsch, S. Vidoni, F. Stein, F. Funke, M. Noltemeyer and A. de Meijere, J. Chem. Soc., Chem. Commun., 1994, 1679; (h) C. Bouancheau, A. Parlier, M. Rudler, H. Rudler, J. Vaissermann and J.-C. Daran, Organometallics, 1994, 13, 4708; (i) J. R. Knorr and T. L. Brown, Organometallics, 1994, 13, 2178; (j) W. D. Wulff, A. M. Gilbert, R. P. Hsung and A. Rahm, J. Org. Chem., 1995, 60, 4566.
18. For discussions of, and recent citations to mechanistic issues, see (a) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell and J. Clardy, Organometallics, 1994, 13, 102; (b) J. Christoffers and K. H. Dötz, Chem. Ber., 1995, 128, 157; (c) J. W. Herndon and A. Hayford, Organometallics, 1995, 14, 1556; (d) M. F. Gross and M. G. Finn, J. Am. Chem. Soc., 1994, 116, 10921; (e) J. Barluenga, F. Aznar, A. Martin, S. Garcia-Granda and E. Perez-Carreno, J. Am. Chem. Soc., 1994, 116, 11191; (f) D. F. Harvey, E. M. Grenzer and P. K. Gantzel, J. Am. Chem. Soc., 1994, 116, 6719; (g) M. Duetsch, S. Vidoni, F. Stein, F. Funke, M. Noltemeyer and A. de Meijere, J. Chem. Soc., Chem. Commun., 1994, 1679; (h) C. Bouancheau, A. Parlier, M. Rudler, H. Rudler, J. Vaissermann and J.-C. Daran, Organometallics, 1994, 13, 4708; (i) J. R. Knorr and T. L. Brown, Organometallics, 1994, 13, 2178; (j) W. D. Wulff, A. M. Gilbert, R. P. Hsung and A. Rahm, J. Org. Chem., 1995, 60, 4566.
19. For discussions of, and recent citations to mechanistic issues, see (a) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell and J. Clardy, Organometallics, 1994, 13, 102; (b) J. Christoffers and K. H. Dötz, Chem. Ber., 1995, 128, 157; (c) J. W. Herndon and A. Hayford, Organometallics, 1995, 14, 1556; (d) M. F. Gross and M. G. Finn, J. Am. Chem. Soc., 1994, 116, 10921; (e) J. Barluenga, F. Aznar, A. Martin, S. Garcia-Granda and E. Perez-Carreno, J. Am. Chem. Soc., 1994, 116, 11191; (f) D. F. Harvey, E. M. Grenzer and P. K. Gantzel, J. Am. Chem. Soc., 1994, 116, 6719; (g) M. Duetsch, S. Vidoni, F. Stein, F. Funke, M. Noltemeyer and A. de Meijere, J. Chem. Soc., Chem. Commun., 1994, 1679; (h) C. Bouancheau, A. Parlier, M. Rudler, H. Rudler, J. Vaissermann and J.-C. Daran, Organometallics, 1994, 13, 4708; (i) J. R. Knorr and T. L. Brown, Organometallics, 1994, 13, 2178; (j) W. D. Wulff, A. M. Gilbert, R. P. Hsung and A. Rahm, J. Org. Chem., 1995, 60, 4566.
20. For discussions of, and recent citations to mechanistic issues, see (a) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell and J. Clardy, Organometallics, 1994, 13, 102; (b) J. Christoffers and K. H. Dötz, Chem. Ber., 1995, 128, 157; (c) J. W. Herndon and A. Hayford, Organometallics, 1995, 14, 1556; (d) M. F. Gross and M. G. Finn, J. Am. Chem. Soc., 1994, 116, 10921; (e) J. Barluenga, F. Aznar, A. Martin, S. Garcia-Granda and E. Perez-Carreno, J. Am. Chem. Soc., 1994, 116, 11191; (f) D. F. Harvey, E. M. Grenzer and P. K. Gantzel, J. Am. Chem. Soc., 1994, 116, 6719; (g) M. Duetsch, S. Vidoni, F. Stein, F. Funke, M. Noltemeyer and A. de Meijere, J. Chem. Soc., Chem. Commun., 1994, 1679; (h) C. Bouancheau, A. Parlier, M. Rudler, H. Rudler, J. Vaissermann and J.-C. Daran, Organometallics, 1994, 13, 4708; (i) J. R. Knorr and T. L. Brown, Organometallics, 1994, 13, 2178; (j) W. D. Wulff, A. M. Gilbert, R. P. Hsung and A. Rahm, J. Org. Chem., 1995, 60, 4566.
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