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Volumn 621, Issue 1-2, 2001, Pages 89-102

Part III. COD versus NBD precatalysts. Dramatic difference in the asymmetric hydrogenation of prochiral olefins with five-membered diphosphine Rh-hydrogenation catalysts

Author keywords

[No Author keywords available]

Indexed keywords

GADUS MORHUA;

EID: 0002955926     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00756-7     Document Type: Article
Times cited : (74)

References (99)
  • 1
    • 0000701744 scopus 로고    scopus 로고
    • Hydrogenation of functionalized carbon-carbon double bonds
    • E.N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Springer, Berlin, Chapter 5.1
    • (a) J.M. Brown, Hydrogenation of functionalized carbon-carbon double bonds. In: E.N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999, Chapter 5.1, pp. 121-182.
    • (1999) Comprehensive Asymmetric Catalysis , pp. 121-182
    • Brown, J.M.1
  • 3
    • 0002944531 scopus 로고    scopus 로고
    • Unnatural α-amino acids, via asymmetric hydrogenation of enamides
    • M. Beller, C. Bolm (Eds.), Wiley-VCH, Weinheim, Chapter 1.1.2
    • (c) M.J. Burk, F. Bienewald, Unnatural α-amino acids, via asymmetric hydrogenation of enamides. In: M. Beller, C. Bolm (Eds.), Transition Metals for Organic Synthesis, vol. I, Wiley-VCH, Weinheim, 1998, Chapter 1.1.2, pp. 13-25.
    • (1998) Transition Metals for Organic Synthesis , vol.1 , pp. 13-25
    • Burk, M.J.1    Bienewald, F.2
  • 4
    • 0000227138 scopus 로고    scopus 로고
    • Hydrogenation
    • B. Cornils, W.A. Herrmann (Eds.), VCH, Weinheim, Chapter 2.2
    • (d) H. Brunner, Hydrogenation. In: B. Cornils, W.A. Herrmann (Eds.), Applied Homogeneous Catalysis with Organometallic Compounds, vols. I and II, VCH, Weinheim, 1996, Chapter 2.2, pp. 201-219.
    • (1996) Applied Homogeneous Catalysis with Organometallic Compounds , vol.1-2 , pp. 201-219
    • Brunner, H.1
  • 7
    • 0001844246 scopus 로고
    • Asymmetric hydrogenation
    • I. Ojima (Ed.), VCH, New York, Chapter 1
    • (g) H. Takaya, T. Ohta, R. Noyori, Asymmetric hydrogenation. In: I. Ojima (Ed.), Catalytic Asymmetric Synthesis, VCH, New York, 1993, Chapter 1, pp. 1-39.
    • (1993) Catalytic Asymmetric Synthesis , pp. 1-39
    • Takaya, H.1    Ohta, T.2    Noyori, R.3
  • 20
    • 0345990427 scopus 로고    scopus 로고
    • cis-Cyclo-octene (COE) and/or cyclo-octane (COA) as well as norbornene (NBE) and/or norbornane (NBA) resulted as hydrogenation product when COD or NBD was used
    • cis-Cyclo-octene (COE) and/or cyclo-octane (COA) as well as norbornene (NBE) and/or norbornane (NBA) resulted as hydrogenation product when COD or NBD was used.
  • 22
    • 0345990428 scopus 로고    scopus 로고
    • note
    • Substrate inhibition as the cause for the observed induction period can be ruled out. The induction periods also cannot be caused by neglecting to add additional hydrogen. For a substrate/precatalyst ratio of 100, there is an error of 2% expected for the complete hydrogenation of the olefin to the saturated product distributed over the entire gas uptake curve.
  • 23
    • 0001537653 scopus 로고
    • (a) U. Nagel, T. Krink, Angew. Chem. 105 (1993) 1099; Angew. Chem. Int. Ed. Engl. 32 (1993) 1052.
    • (1993) Angew. Chem. , vol.105 , pp. 1099
    • Nagel, U.1    Krink, T.2
  • 24
    • 33748810705 scopus 로고
    • (a) U. Nagel, T. Krink, Angew. Chem. 105 (1993) 1099; Angew. Chem. Int. Ed. Engl. 32 (1993) 1052.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1052
  • 28
    • 0000673036 scopus 로고    scopus 로고
    • D.G. Blackmond, T. Rosner, T. Neugebauer, M. Reetz, Angew. Chem. 111 (1999) 2333; Angew. Chem. Int. Ed. Engl. 38 (1999) 2196. 1:1 mixtures of the diastereomeric catalysts led to unexpectedly high enantioselectivities for the hydrogenation of dimethyl itaconate. These are the results of the various induction periods for the diastereomeric COD employed catalysts, so that the end effect is that the hydrogenation at first runs via a diastereomeric catalyst.
    • (1999) Angew. Chem. , vol.111 , pp. 2333
    • Blackmond, D.G.1    Rosner, T.2    Neugebauer, T.3    Reetz, M.4
  • 29
    • 0033516889 scopus 로고    scopus 로고
    • D.G. Blackmond, T. Rosner, T. Neugebauer, M. Reetz, Angew. Chem. 111 (1999) 2333; Angew. Chem. Int. Ed. Engl. 38 (1999) 2196. 1:1 mixtures of the diastereomeric catalysts led to unexpectedly high enantioselectivities for the hydrogenation of dimethyl itaconate. These are the results of the various induction periods for the diastereomeric COD employed catalysts, so that the end effect is that the hydrogenation at first runs via a diastereomeric catalyst.
    • (1999) Angew. Chem. Int. Ed. Engl. , vol.38 , pp. 2196
  • 34
    • 84985598655 scopus 로고
    • (a) H. Brunner, W. Pieronczyk, Angew. Chem. 91 (1979) 655; Angew. Chem. Int. Ed. Engl. 18 (1979) 620.
    • (1979) Angew. Chem. Int. Ed. Engl. , vol.18 , pp. 620
  • 35
    • 84982059863 scopus 로고
    • (b) H. Brunner, W. Pieronczyk, B. Schonhammer, K. Streng, I. Bernal, J. Korp, Chem. Ber. 114 (1981) 1137. For problems encountered with RENORHOS refer to [31b]. A hydroxy derivative of NORPHOS is described in J. Ward, A. Börner, H.B. Kagan, Tetrahedron: Asymm. 3 (1992) 849.
    • (1981) Chem. Ber. , vol.114 , pp. 1137
    • Brunner, H.1    Pieronczyk, W.2    Schonhammer, B.3    Streng, K.4    Bernal, I.5    Korp, J.6
  • 36
    • 0026777783 scopus 로고
    • (b) H. Brunner, W. Pieronczyk, B. Schonhammer, K. Streng, I. Bernal, J. Korp, Chem. Ber. 114 (1981) 1137. For problems encountered with RENORHOS refer to [31b]. A hydroxy derivative of NORPHOS is described in J. Ward, A. Börner, H.B. Kagan, Tetrahedron: Asymm. 3 (1992) 849.
    • (1992) Tetrahedron: Asymm. , vol.3 , pp. 849
    • Ward, J.1    Börner, A.2    Kagan, H.B.3
  • 39
    • 0346621638 scopus 로고    scopus 로고
    • note
    • Since the partial reaction order for hydrogen, for the asymmetric reaction as well as for the diolefin hydrogenation, is one [4c] analogous results will also be obtained with other pressures.
  • 48
    • 0000060624 scopus 로고    scopus 로고
    • (i) J. Albrecht, U. Nagel, Angew. Chem. 108 (1996) 444; Angew. Chem. Int. Ed. Engl. 35 (1996) 407.
    • (1996) Angew. Chem. , vol.108 , pp. 444
    • Albrecht, J.1    Nagel, U.2
  • 49
    • 33748237712 scopus 로고    scopus 로고
    • (i) J. Albrecht, U. Nagel, Angew. Chem. 108 (1996) 444; Angew. Chem. Int. Ed. Engl. 35 (1996) 407.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 407
  • 68
    • 0032482106 scopus 로고    scopus 로고
    • Q. Jiang, Y. Jiang, D. Xiao, P. Cao, X. Zhang, Angew. Chem. 110 (1998) 1203; Angew. Chem. Int. Ed. Engl. 37 (1998) 1100.
    • (1998) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 1100
  • 74
    • 0347251467 scopus 로고    scopus 로고
    • note
    • The results obtained in the NMR tube correspond approximately to those determined in the standard hydrogenation vessel at 15.0°C (total reaction time 45 min, 99.5% ee (5) 48% COD).
  • 86
    • 0027397575 scopus 로고
    • (f) S.K. Armstrong, J.M. Brown, M.J. Burk, Tetrahedron Lett. 34 (1993) 879. Reviews on structures of chiral rhodium complexes are found in J.M. Brown, P.L. Evans, Tetrahedron 44 (1988) 4905 or H. Brunner, A. Winter, J. Breu, J. Organomet. Chem. 553 (1998) 285.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 879
    • Armstrong, S.K.1    Brown, J.M.2    Burk, M.J.3
  • 87
    • 0000634303 scopus 로고
    • (f) S.K. Armstrong, J.M. Brown, M.J. Burk, Tetrahedron Lett. 34 (1993) 879. Reviews on structures of chiral rhodium complexes are found in J.M. Brown, P.L. Evans, Tetrahedron 44 (1988) 4905 or H. Brunner, A. Winter, J. Breu, J. Organomet. Chem. 553 (1998) 285.
    • (1988) Tetrahedron , vol.44 , pp. 4905
    • Brown, J.M.1    Evans, P.L.2
  • 88
    • 0001115955 scopus 로고    scopus 로고
    • (f) S.K. Armstrong, J.M. Brown, M.J. Burk, Tetrahedron Lett. 34 (1993) 879. Reviews on structures of chiral rhodium complexes are found in J.M. Brown, P.L. Evans, Tetrahedron 44 (1988) 4905 or H. Brunner, A. Winter, J. Breu, J. Organomet. Chem. 553 (1998) 285.
    • (1998) J. Organomet. Chem. , vol.553 , pp. 285
    • Brunner, H.1    Winter, A.2    Breu, J.3
  • 89
    • 0345770944 scopus 로고    scopus 로고
    • Emst-Moritz-Arndt-Universität, Greifswald
    • D. Heller, Habilitationsschrift, Emst-Moritz-Arndt-Universität, Greifswald, 1998.
    • (1998) Habilitationsschrift
    • Heller, D.1
  • 91
    • 0347881977 scopus 로고    scopus 로고
    • in press
    • It must be mentioned here that the NBD complexes of ligands with cyclohexyl instead of phenyl residues (DCPB 1,4-bis(dicyclohexylphosphino)butane, DCPE 1,2 bis(dicyclohexylphosphino)ethane) are still the more reactive species but also exhibit greater distortions from the square-planar arrangement (R. Kempe, A. Spannenberg, D. Heller, Z. Kristallogr. (in press). R. Kempe, A. Spannenberg, H.-J. Drexler, D. Heller, Z. Kristallogr. (in press)). The role of the cyclohexyl ligand in such situations is still unexplored.
    • Z. Kristallogr.
    • Kempe, R.1    Spannenberg, A.2    Heller, D.3
  • 92
    • 0347881977 scopus 로고    scopus 로고
    • in press
    • It must be mentioned here that the NBD complexes of ligands with cyclohexyl instead of phenyl residues (DCPB 1,4-bis(dicyclohexylphosphino)butane, DCPE 1,2 bis(dicyclohexylphosphino)ethane) are still the more reactive species but also exhibit greater distortions from the square-planar arrangement (R. Kempe, A. Spannenberg, D. Heller, Z. Kristallogr. (in press). R. Kempe, A. Spannenberg, H.-J. Drexler, D. Heller, Z. Kristallogr. (in press)). The role of the cyclohexyl ligand in such situations is still unexplored.
    • Z. Kristallogr.
    • Kempe, R.1    Spannenberg, A.2    Drexler, H.-J.3    Heller, D.4
  • 96
    • 0030601306 scopus 로고    scopus 로고
    • The problem of induction periods is by no means restricted to asymmetric hydrogenation, but is a general phenomenon in homogeneous catalysis whenever precatalysts are used. This has been shown for the photocatalysed [2+2+2] cycloaddition of alkynes with nitriles, for instance: B. Heller, D. Heller, G. Oehme, J. Mol. Catal. A 110 (1996) 211.
    • (1996) J. Mol. Catal. A , vol.110 , pp. 211
    • Heller, B.1    Heller, D.2    Oehme, G.3
  • 98
    • 0004150157 scopus 로고    scopus 로고
    • University of Göttingen, Germany
    • G.M. Sheldrick, SHELXS-97, University of Göttingen, Germany, 1997.
    • (1997) SHELXS-97
    • Sheldrick, G.M.1
  • 99
    • 0004150157 scopus 로고    scopus 로고
    • University of Göttingen, Germany
    • G.M. Sheldrick, SHELXL-97, University of Göttingen, Germany, 1997.
    • (1997) SHELXL-97
    • Sheldrick, G.M.1


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