A new class of Rh(III) catalyst containing an aminoalcohol tethered to a tetramethylcyclopentadienyl group for asymmetric transfer hydrogenation of ketones

Tetrahedron Letters

Volumn 45, Issue 4, 2004, Pages 843-846

  Cross, David J ^a   Houson, Ian ^b   Kawamoto, Aparecida M ^a,c   Wills, Martin ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b Avecia Biologics Limited   (United Kingdom)

^c Brazilian Space Aero Institute   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; AMINOALCOHOL; CYCLOPENTADIENE DERIVATIVE; KETONE DERIVATIVE; RHODIUM DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; CHIRALITY; DEGRADATION KINETICS; HYDROGENATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0348048821     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.024     Document Type: Article

References (30)

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9. Palmer M.J., Wills M. Tetrahedron: Asymmetry. 10:1999;2045 Noyori R., Hashiguchi S. Acc. Chem. Res. 30:1997;97 Wills M., Gamble M., Palmer M.J., Smith A.R.C., Studley J.R., Kenny J.A. J. Mol. Catal. A: Chem. 146:1999;139 Kenny J.A., Palmer M.J., Smith A.R.C., Walsgrove T., Wills M. Synlett. 1999;1615 Wills M., Palmer M.J., Smith A.R.C., Kenny J.A., Walsgrove T. Molecules. 5:2000;1 Kenny J.A., Versluis K., Heck A.J.R., Walsgrove T., Wills M. Chem. Commun. 2000;99 Kawamoto A.M., Wills M. Tetrahedron: Asymmetry. 11:2000;3257 Kawamoto A.M., Wills M. J. Chem. Soc., Perkin Trans. 1. 2001;1916 Hannedouche J., Kenny J.A., Walsgrove T., Wills M. Synlett. 2002;263 Kenny J.A., Palmer M.J., Walsgrove T., Kawamoto A.M., Wills M. J. Chem. Soc., Perkin Trans. 1. 2002;416 Cross D.J., Kenny J.A., Houston I., Campbell L., Walsgrove T., Wills M. Tetrahedron: Asymmetry. 12:2001;1801 Alcock N.W., Mann I., Peach P., Wills M. Tetrahedron: Asymmetry. 13:2002;2485.
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17. Takehara J., Hashiguchi S., Fujii A., Inoue S.-I., Ikariya T., Noyori R. Chem. Commun. 1996;233 Palmer M., Walsgrove T., Wills M. J. Org. Chem. 62:1997;5226 Nordin S.J.M., Roth P., Tarnai T., Alonso D.A., Brandt P., Andersson P.G. Chem. Eur. J. 7:2001;1431 Everaere K., Mortreaux A., Bulliard M., Brussee J., van der Gen A., Nowogrocki G., Carpentier J.-F. Eur. J. Org. Chem. 2001;275 Hennig M., Puntener K., Scalone M. Tetrahedron: Asymmetry. 11: 2000;1849 Blacker, A. J.; Mellor, B. J. (Avecia/Zeneca), WO9842643 A1, 1998 Fujii A., Hashiguchi S., Uematsu N., Ikariya T., Noyori R. J. Am. Chem. Soc. 118:1996;2521 Hashiguchi S., Fujii A., Takehara J., Ikariya T., Noyori R. J. Am. Chem. Soc. 117:1995;7562 Haack K.-J., Hashiguchi S., Fujii A., Ikariya T., Noyori R. Angew. Chem., Int. Ed. 36:1997;285 Mashima K., Abe T., Tani K. Chem. Lett. 1998;1199 Murata K., Ikariya T., Noyori R. J. Org. Chem. 64:1999;2186.
18. Takehara J., Hashiguchi S., Fujii A., Inoue S.-I., Ikariya T., Noyori R. Chem. Commun. 1996;233 Palmer M., Walsgrove T., Wills M. J. Org. Chem. 62:1997;5226 Nordin S.J.M., Roth P., Tarnai T., Alonso D.A., Brandt P., Andersson P.G. Chem. Eur. J. 7:2001;1431 Everaere K., Mortreaux A., Bulliard M., Brussee J., van der Gen A., Nowogrocki G., Carpentier J.-F. Eur. J. Org. Chem. 2001;275 Hennig M., Puntener K., Scalone M. Tetrahedron: Asymmetry. 11: 2000;1849 Blacker, A. J.; Mellor, B. J. (Avecia/Zeneca), WO9842643 A1, 1998 Fujii A., Hashiguchi S., Uematsu N., Ikariya T., Noyori R. J. Am. Chem. Soc. 118:1996;2521 Hashiguchi S., Fujii A., Takehara J., Ikariya T., Noyori R. J. Am. Chem. Soc. 117:1995;7562 Haack K.-J., Hashiguchi S., Fujii A., Ikariya T., Noyori R. Angew. Chem., Int. Ed. 36:1997;285 Mashima K., Abe T., Tani K. Chem. Lett. 1998;1199 Murata K., Ikariya T., Noyori R. J. Org. Chem. 64:1999;2186.
19. Takehara J., Hashiguchi S., Fujii A., Inoue S.-I., Ikariya T., Noyori R. Chem. Commun. 1996;233 Palmer M., Walsgrove T., Wills M. J. Org. Chem. 62:1997;5226 Nordin S.J.M., Roth P., Tarnai T., Alonso D.A., Brandt P., Andersson P.G. Chem. Eur. J. 7:2001;1431 Everaere K., Mortreaux A., Bulliard M., Brussee J., van der Gen A., Nowogrocki G., Carpentier J.-F. Eur. J. Org. Chem. 2001;275 Hennig M., Puntener K., Scalone M. Tetrahedron: Asymmetry. 11: 2000;1849 Blacker, A. J.; Mellor, B. J. (Avecia/Zeneca), WO9842643 A1, 1998 Fujii A., Hashiguchi S., Uematsu N., Ikariya T., Noyori R. J. Am. Chem. Soc. 118:1996;2521 Hashiguchi S., Fujii A., Takehara J., Ikariya T., Noyori R. J. Am. Chem. Soc. 117:1995;7562 Haack K.-J., Hashiguchi S., Fujii A., Ikariya T., Noyori R. Angew. Chem., Int. Ed. 36:1997;285 Mashima K., Abe T., Tani K. Chem. Lett. 1998;1199 Murata K., Ikariya T., Noyori R. J. Org. Chem. 64:1999;2186.
20. Takehara J., Hashiguchi S., Fujii A., Inoue S.-I., Ikariya T., Noyori R. Chem. Commun. 1996;233 Palmer M., Walsgrove T., Wills M. J. Org. Chem. 62:1997;5226 Nordin S.J.M., Roth P., Tarnai T., Alonso D.A., Brandt P., Andersson P.G. Chem. Eur. J. 7:2001;1431 Everaere K., Mortreaux A., Bulliard M., Brussee J., van der Gen A., Nowogrocki G., Carpentier J.-F. Eur. J. Org. Chem. 2001;275 Hennig M., Puntener K., Scalone M. Tetrahedron: Asymmetry. 11: 2000;1849 Blacker, A. J.; Mellor, B. J. (Avecia/Zeneca), WO9842643 A1, 1998 Fujii A., Hashiguchi S., Uematsu N., Ikariya T., Noyori R. J. Am. Chem. Soc. 118:1996;2521 Hashiguchi S., Fujii A., Takehara J., Ikariya T., Noyori R. J. Am. Chem. Soc. 117:1995;7562 Haack K.-J., Hashiguchi S., Fujii A., Ikariya T., Noyori R. Angew. Chem., Int. Ed. 36:1997;285 Mashima K., Abe T., Tani K. Chem. Lett. 1998;1199 Murata K., Ikariya T., Noyori R. J. Org. Chem. 64:1999;2186.
21. Takehara J., Hashiguchi S., Fujii A., Inoue S.-I., Ikariya T., Noyori R. Chem. Commun. 1996;233 Palmer M., Walsgrove T., Wills M. J. Org. Chem. 62:1997;5226 Nordin S.J.M., Roth P., Tarnai T., Alonso D.A., Brandt P., Andersson P.G. Chem. Eur. J. 7:2001;1431 Everaere K., Mortreaux A., Bulliard M., Brussee J., van der Gen A., Nowogrocki G., Carpentier J.-F. Eur. J. Org. Chem. 2001;275 Hennig M., Puntener K., Scalone M. Tetrahedron: Asymmetry. 11: 2000;1849 Blacker, A. J.; Mellor, B. J. (Avecia/Zeneca), WO9842643 A1, 1998 Fujii A., Hashiguchi S., Uematsu N., Ikariya T., Noyori R. J. Am. Chem. Soc. 118:1996;2521 Hashiguchi S., Fujii A., Takehara J., Ikariya T., Noyori R. J. Am. Chem. Soc. 117:1995;7562 Haack K.-J., Hashiguchi S., Fujii A., Ikariya T., Noyori R. Angew. Chem., Int. Ed. 36:1997;285 Mashima K., Abe T., Tani K. Chem. Lett. 1998;1199 Murata K., Ikariya T., Noyori R. J. Org. Chem. 64:1999;2186.
22. Takehara J., Hashiguchi S., Fujii A., Inoue S.-I., Ikariya T., Noyori R. Chem. Commun. 1996;233 Palmer M., Walsgrove T., Wills M. J. Org. Chem. 62:1997;5226 Nordin S.J.M., Roth P., Tarnai T., Alonso D.A., Brandt P., Andersson P.G. Chem. Eur. J. 7:2001;1431 Everaere K., Mortreaux A., Bulliard M., Brussee J., van der Gen A., Nowogrocki G., Carpentier J.-F. Eur. J. Org. Chem. 2001;275 Hennig M., Puntener K., Scalone M. Tetrahedron: Asymmetry. 11: 2000;1849 Blacker, A. J.; Mellor, B. J. (Avecia/Zeneca), WO9842643 A1, 1998 Fujii A., Hashiguchi S., Uematsu N., Ikariya T., Noyori R. J. Am. Chem. Soc. 118:1996;2521 Hashiguchi S., Fujii A., Takehara J., Ikariya T., Noyori R. J. Am. Chem. Soc. 117:1995;7562 Haack K.-J., Hashiguchi S., Fujii A., Ikariya T., Noyori R. Angew. Chem., Int. Ed. 36:1997;285 Mashima K., Abe T., Tani K. Chem. Lett. 1998;1199 Murata K., Ikariya T., Noyori R. J. Org. Chem. 64:1999;2186.
23. Alonso D.A., Brandt A., Nordin S.J.M., Andersson P.G. J. Am. Chem. Soc. 121:1999;9580 Yamakawa M., Ito H., Noyori R. J. Am. Chem. Soc. 122:2000;1466 Yamakawa M., Yamada I., Noyori R. Angew. Chem., Int. Ed. Engl. 40:2001;2818.
24. Alonso D.A., Brandt A., Nordin S.J.M., Andersson P.G. J. Am. Chem. Soc. 121:1999;9580 Yamakawa M., Ito H., Noyori R. J. Am. Chem. Soc. 122:2000;1466 Yamakawa M., Yamada I., Noyori R. Angew. Chem., Int. Ed. Engl. 40:2001;2818.
25. Alonso D.A., Brandt A., Nordin S.J.M., Andersson P.G. J. Am. Chem. Soc. 121:1999;9580 Yamakawa M., Ito H., Noyori R. J. Am. Chem. Soc. 122:2000;1466 Yamakawa M., Yamada I., Noyori R. Angew. Chem., Int. Ed. Engl. 40:2001;2818.
26. Yamakawa M.I., Yamada I., Noyori R. Angew. Chem., Int. Ed. 40:2001;2818.
27. For an example of a tethered Cp/Ru system see: Brunner H., Valerio C., Zabel M. New J. Chem. 24:2000;275.
28. 29 ClNORh=498.10254, found 498.10664.
29. N-2-(2,3,4,5-Tetramethylcyclopentadienyl)benzyl-(L)-norephedrine rhodium(III) chloride 6 catalysed transfer hydrogenation of acetophenone; typical procedure (5 mol %). N-2-(2,3,4,5-Tetramethylcyclopentadienyl)benzyl-(L) -norephedrine rhodium(III) chloride 6 (0.025 g, 0.05 mmol) was stirred in acetophenone (0.120 g, 1 mmol) under nitrogen in a flame dried Schlenk tube for 30 min. Degassed propan-2-ol (10 mL) was added and the reaction mixture was stirred for 2 h. Sodium tert-butoxide (1.0 mL, 0.1 M solution in propan-2-ol) was added. Samples were filtered through silica, concentrated under reduced pressure and analysed by NMR and HPLC. After 2 min the conversion was 78.2% and ee 73.5% by HPLC analysis [Chiracel OD, hexane/ethanol=95:5 (1.0 mL/min)], R isomer 8.30 min, S isomer 9.35 min.
30. Fletcher D.A., McMeeking R.F., Parkin D. J. Chem. Inf. Comput. Sci. 36:1996;746.