Enantioselective Metal-catalyzed Baeyer-Villiger Oxidation of Cyclobutanones

Synlett

Volumn 1997, Issue 10, 1997, Pages 1151-1152

  Bolm, Carsten ^a   Luong, T Kim Khanh ^a   Schlingloff, Gunther ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011306159     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-977     Document Type: Article

References (33)

1. Baeyer, A.; Villiger, V. Ber. 1899, 32, 3625.
2. For recent reviews of the Baeyer-Villiger oxidation see: Krow, G. R. Org. React. 1993, 43, 251. Krow, G. R. In Comprehensive Organic Synthesis, Vol. 7; Trost B. M.; Fleming, I., Ed.; Pergamon: Oxford, 1991; p 671. Bolm, C. In Advances in Catalytic Processes, Doyle, M. P. Ed., JAI Press: Greenwich, in press.
3. For recent reviews of the Baeyer-Villiger oxidation see: Krow, G. R. Org. React. 1993, 43, 251. Krow, G. R. In Comprehensive Organic Synthesis, Vol. 7; Trost B. M.; Fleming, I., Ed.; Pergamon: Oxford, 1991; p 671. Bolm, C. In Advances in Catalytic Processes, Doyle, M. P. Ed., JAI Press: Greenwich, in press.
4. For recent reviews of the Baeyer-Villiger oxidation see: Krow, G. R. Org. React. 1993, 43, 251. Krow, G. R. In Comprehensive Organic Synthesis, Vol. 7; Trost B. M.; Fleming, I., Ed.; Pergamon: Oxford, 1991; p 671. Bolm, C. In Advances in Catalytic Processes, Doyle, M. P. Ed., JAI Press: Greenwich, in press.
5. Roberts, S. M.; Turner, N. J.; Willetts, A. J. Chimia 1993, 47, 85. Azerad, R. Bull. Chem. Soc. Fr. 1995, 132, 17. Biotransformations in Organic Chemistry, Faber, K., Ed.; Springer-Verlag: Heidelberg, 1992. Alphand, V.; Furstoss, R. In Enzyme Catalysis in Organic Synthesis, Drauz K.; Waldmann, H., Ed.; VCH: Weinheim, 1995; p 745.
6. Roberts, S. M.; Turner, N. J.; Willetts, A. J. Chimia 1993, 47, 85. Azerad, R. Bull. Chem. Soc. Fr. 1995, 132, 17. Biotransformations in Organic Chemistry, Faber, K., Ed.; Springer-Verlag: Heidelberg, 1992. Alphand, V.; Furstoss, R. In Enzyme Catalysis in Organic Synthesis, Drauz K.; Waldmann, H., Ed.; VCH: Weinheim, 1995; p 745.
7. Roberts, S. M.; Turner, N. J.; Willetts, A. J. Chimia 1993, 47, 85. Azerad, R. Bull. Chem. Soc. Fr. 1995, 132, 17. Biotransformations in Organic Chemistry, Faber, K., Ed.; Springer-Verlag: Heidelberg, 1992. Alphand, V.; Furstoss, R. In Enzyme Catalysis in Organic Synthesis, Drauz K.; Waldmann, H., Ed.; VCH: Weinheim, 1995; p 745.
8. Roberts, S. M.; Turner, N. J.; Willetts, A. J. Chimia 1993, 47, 85. Azerad, R. Bull. Chem. Soc. Fr. 1995, 132, 17. Biotransformations in Organic Chemistry, Faber, K., Ed.; Springer-Verlag: Heidelberg, 1992. Alphand, V.; Furstoss, R. In Enzyme Catalysis in Organic Synthesis, Drauz K.; Waldmann, H., Ed.; VCH: Weinheim, 1995; p 745.
9. Early review: Walsh, C. T.; Chen, Y. -C. J. Angew. Chem. 1988, 100, 342; Angew. Chem. Int. Ed. Engl. 1988, 27, 333. Selected recent references: Lemoult, S. C.; Richardson, P. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. I 1995, 89. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Wright, M. A.; Taylor, I. N.; Roberts, S. M.; Wan, P. W. H.; Grogan, G.; Pedragosa-Moreau, S.; Willetts, A. J. J. Chem. Soc., Chem. Commun. 1996, 2333. Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P. F.; Roberts, S. M.; Willetts, A. J.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans I 1995, 2527. Petit, F.; Furstoss, R. Tetrahedron: Asymmetry 1993, 4, 1341. Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts A. J. J. Chem. Soc., Perkin Trans I 1996, 1867. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145 and references therein.
10. Early review: Walsh, C. T.; Chen, Y. -C. J. Angew. Chem. 1988, 100, 342; Angew. Chem. Int. Ed. Engl. 1988, 27, 333. Selected recent references: Lemoult, S. C.; Richardson, P. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. I 1995, 89. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Wright, M. A.; Taylor, I. N.; Roberts, S. M.; Wan, P. W. H.; Grogan, G.; Pedragosa-Moreau, S.; Willetts, A. J. J. Chem. Soc., Chem. Commun. 1996, 2333. Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P. F.; Roberts, S. M.; Willetts, A. J.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans I 1995, 2527. Petit, F.; Furstoss, R. Tetrahedron: Asymmetry 1993, 4, 1341. Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts A. J. J. Chem. Soc., Perkin Trans I 1996, 1867. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145 and references therein.
11. Early review: Walsh, C. T.; Chen, Y. -C. J. Angew. Chem. 1988, 100, 342; Angew. Chem. Int. Ed. Engl. 1988, 27, 333. Selected recent references: Lemoult, S. C.; Richardson, P. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. I 1995, 89. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Wright, M. A.; Taylor, I. N.; Roberts, S. M.; Wan, P. W. H.; Grogan, G.; Pedragosa-Moreau, S.; Willetts, A. J. J. Chem. Soc., Chem. Commun. 1996, 2333. Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P. F.; Roberts, S. M.; Willetts, A. J.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans I 1995, 2527. Petit, F.; Furstoss, R. Tetrahedron: Asymmetry 1993, 4, 1341. Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts A. J. J. Chem. Soc., Perkin Trans I 1996, 1867. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145 and references therein.
12. Early review: Walsh, C. T.; Chen, Y. -C. J. Angew. Chem. 1988, 100, 342; Angew. Chem. Int. Ed. Engl. 1988, 27, 333. Selected recent references: Lemoult, S. C.; Richardson, P. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. I 1995, 89. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Wright, M. A.; Taylor, I. N.; Roberts, S. M.; Wan, P. W. H.; Grogan, G.; Pedragosa-Moreau, S.; Willetts, A. J. J. Chem. Soc., Chem. Commun. 1996, 2333. Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P. F.; Roberts, S. M.; Willetts, A. J.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans I 1995, 2527. Petit, F.; Furstoss, R. Tetrahedron: Asymmetry 1993, 4, 1341. Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts A. J. J. Chem. Soc., Perkin Trans I 1996, 1867. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145 and references therein.
13. Early review: Walsh, C. T.; Chen, Y. -C. J. Angew. Chem. 1988, 100, 342; Angew. Chem. Int. Ed. Engl. 1988, 27, 333. Selected recent references: Lemoult, S. C.; Richardson, P. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. I 1995, 89. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Wright, M. A.; Taylor, I. N.; Roberts, S. M.; Wan, P. W. H.; Grogan, G.; Pedragosa-Moreau, S.; Willetts, A. J. J. Chem. Soc., Chem. Commun. 1996, 2333. Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P. F.; Roberts, S. M.; Willetts, A. J.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans I 1995, 2527. Petit, F.; Furstoss, R. Tetrahedron: Asymmetry 1993, 4, 1341. Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts A. J. J. Chem. Soc., Perkin Trans I 1996, 1867. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145 and references therein.
14. Early review: Walsh, C. T.; Chen, Y. -C. J. Angew. Chem. 1988, 100, 342; Angew. Chem. Int. Ed. Engl. 1988, 27, 333. Selected recent references: Lemoult, S. C.; Richardson, P. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. I 1995, 89. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Wright, M. A.; Taylor, I. N.; Roberts, S. M.; Wan, P. W. H.; Grogan, G.; Pedragosa-Moreau, S.; Willetts, A. J. J. Chem. Soc., Chem. Commun. 1996, 2333. Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P. F.; Roberts, S. M.; Willetts, A. J.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans I 1995, 2527. Petit, F.; Furstoss, R. Tetrahedron: Asymmetry 1993, 4, 1341. Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts A. J. J. Chem. Soc., Perkin Trans I 1996, 1867. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145 and references therein.
15. Early review: Walsh, C. T.; Chen, Y. -C. J. Angew. Chem. 1988, 100, 342; Angew. Chem. Int. Ed. Engl. 1988, 27, 333. Selected recent references: Lemoult, S. C.; Richardson, P. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. I 1995, 89. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Wright, M. A.; Taylor, I. N.; Roberts, S. M.; Wan, P. W. H.; Grogan, G.; Pedragosa-Moreau, S.; Willetts, A. J. J. Chem. Soc., Chem. Commun. 1996, 2333. Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P. F.; Roberts, S. M.; Willetts, A. J.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans I 1995, 2527. Petit, F.; Furstoss, R. Tetrahedron: Asymmetry 1993, 4, 1341. Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts A. J. J. Chem. Soc., Perkin Trans I 1996, 1867. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145 and references therein.
16. Early review: Walsh, C. T.; Chen, Y. -C. J. Angew. Chem. 1988, 100, 342; Angew. Chem. Int. Ed. Engl. 1988, 27, 333. Selected recent references: Lemoult, S. C.; Richardson, P. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. I 1995, 89. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Wright, M. A.; Taylor, I. N.; Roberts, S. M.; Wan, P. W. H.; Grogan, G.; Pedragosa-Moreau, S.; Willetts, A. J. J. Chem. Soc., Chem. Commun. 1996, 2333. Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P. F.; Roberts, S. M.; Willetts, A. J.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans I 1995, 2527. Petit, F.; Furstoss, R. Tetrahedron: Asymmetry 1993, 4, 1341. Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts A. J. J. Chem. Soc., Perkin Trans I 1996, 1867. Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145 and references therein.
17. Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem. 1994, 106, 1944; Angew. Chem. Int. Ed. Engl. 1994, 33, 1848. Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247. Bolm, C.; Schlingloff; G.; Bienewald, F. J. Mol. Cat. 1997, 117, 347.
18. Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem. 1994, 106, 1944; Angew. Chem. Int. Ed. Engl. 1994, 33, 1848. Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247. Bolm, C.; Schlingloff; G.; Bienewald, F. J. Mol. Cat. 1997, 117, 347.
19. Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem. 1994, 106, 1944; Angew. Chem. Int. Ed. Engl. 1994, 33, 1848. Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247. Bolm, C.; Schlingloff; G.; Bienewald, F. J. Mol. Cat. 1997, 117, 347.
20. Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem. 1994, 106, 1944; Angew. Chem. Int. Ed. Engl. 1994, 33, 1848. Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247. Bolm, C.; Schlingloff; G.; Bienewald, F. J. Mol. Cat. 1997, 117, 347.
21. Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442. Strukul, G.; Varagnolo, A.; Pinna, F. J. Mol. Cat. 1997, 117, 413.
22. Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442. Strukul, G.; Varagnolo, A.; Pinna, F. J. Mol. Cat. 1997, 117, 413.
23. Lopp, M.; Paju, A.; Kanger, T.; Pehk, T. Tetrahedron Lett. 1996, 37, 7583.
24. For a very early report on this phenomenon found in a microbiological Baeyer-Villiger type oxidation see: Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 30, 3663.
25. Kagan, H. B. Croatica Chem. Acta 1996, 69, 669.
26. GC and HPLC columns used: Lipodex B, Lipodex D or Chiralcel OD-H, respectively. Peak assignments were confirmed by analyzing samples of racemic product.
27. Helmchen, G.; Nill, G. Angew. Chem. 1979, 91, 66; Angew. Chem. Int. Ed. Engl. 1979, 18, 65. Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans I 1983, 2629.
28. Helmchen, G.; Nill, G. Angew. Chem. 1979, 91, 66; Angew. Chem. Int. Ed. Engl. 1979, 18, 65. Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans I 1983, 2629.
29. Helmchen, G.; Nill, G. Angew. Chem. 1979, 91, 66; Angew. Chem. Int. Ed. Engl. 1979, 18, 65. Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans I 1983, 2629.
30. The absolute configurations of the other lactones described in the Table remained undetermined.
31. Previously, Kelly and coworkers have very elegantly used tricyclic ketone 8 for mapping of the functional active site of Baeyer-Villigerases. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Taylor; I. N.; Wright, M. A. J. Chem. Soc., Chem. Commun. 1995, 729. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Wright, M. A.; Taylor, I. N.; Hibbs, D. E.; Hursthouse, M. B.; Mish'al, A. K.; Roberts, S. M.; Wan, P. W. H.; Grogan; G.; Willetts, A. J. J. Chem. Soc., Perkin Trans I 1995, 2057.
32. Previously, Kelly and coworkers have very elegantly used tricyclic ketone 8 for mapping of the functional active site of Baeyer-Villigerases. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Taylor; I. N.; Wright, M. A. J. Chem. Soc., Chem. Commun. 1995, 729. Kelly, D. R.; Knowles, C. J.; Mahdi, J. G.; Wright, M. A.; Taylor, I. N.; Hibbs, D. E.; Hursthouse, M. B.; Mish'al, A. K.; Roberts, S. M.; Wan, P. W. H.; Grogan; G.; Willetts, A. J. J. Chem. Soc., Perkin Trans I 1995, 2057.
33. For a theoretical investigation of the Baeyer-Villiger reaction: Okuno, Y. Chem. Eur. J. 1997, 3, 212.