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Volumn , Issue , 2008, Pages 995-1027

Enantioselective Alkene Hydrogenation: Monodentate Ligands

Author keywords

Enamides; Methanol; Monodentate ligands; Monophosphoramidites; Phosphines

Indexed keywords


EID: 84891018984     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527619382.ch28     Document Type: Chapter
Times cited : (28)

References (118)
  • 5
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    • Comprehensive Asymmetric Catalysis
    • For an excellent overview of the field of enantioselective hydrogenation, see:, in: E.N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Springer, Berlin, Chapter 5.1
    • For an excellent overview of the field of enantioselective hydrogenation, see: J. M. Brown, in: E.N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999, Vol. 1, Chapter 5.1.
    • (1999) , vol.1
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  • 11
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    • in: J.D. Morrison (Ed.), Academic Press, Inc., Orlando
    • H.B. Kagan., in: J.D. Morrison (Ed.), Asymmetric Synthesis, Academic Press, Inc., Orlando, 1985, Volume 5;
    • (1985) Asymmetric Synthesis , vol.5
    • Kagan, H.B.1
  • 14
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    • Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions
    • (Eds.), Wiley-VCH
    • H.U. Blaser, E. Schmidt (Eds.), Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions, Wiley-VCH, 2004.
    • (2004)
    • Blaser, H.U.1    Schmidt, E.2
  • 17
    • 0033389244 scopus 로고    scopus 로고
    • For a discussion on this topic, see:
    • For a discussion on this topic, see: X. Zhang, Enantiomer 1999, 4, 541.
    • (1999) Enantiomer , vol.4 , pp. 541
    • Zhang, X.1
  • 18
    • 0034079675 scopus 로고    scopus 로고
    • For a review on the use ofchiral mono-dentate phosphines in asymmetric catalysis, see:
    • For a review on the use ofchiral mono-dentate phosphines in asymmetric catalysis, see: F. Lagasse, H.B. Kagan, Chem. Pharm. Bull. 2000, 48, 315.
    • (2000) Chem. Pharm. Bull. , vol.48 , pp. 315
    • Lagasse, F.1    Kagan, H.B.2
  • 19
    • 0035794970 scopus 로고    scopus 로고
    • For a perspective on the use of chiral monodentate phosphorus ligands in en-antioselective olefin hydrogenations see:
    • For a perspective on the use of chiral monodentate phosphorus ligands in en-antioselective olefin hydrogenations see: I.V. Komarov, A. Börner, Angew. Chem. Int. Ed. 2001, 40, 1197.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1197
    • Komarov, I.V.1    Börner, A.2
  • 20
    • 0033537803 scopus 로고    scopus 로고
    • As a forerunner, the development of a new, though less enantioselective, monodentate phosphine ligand was reported
    • As a forerunner, the development of a new, though less enantioselective, monodentate phosphine ligand was reported; F. Guillen, J.-C. Fiaud, Tetrahedron Lett. 1999, 40, 2939.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2939
    • Guillen, F.1    Fiaud, J.-C.2
  • 29
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    • see Ref. 91
    • see Ref. 91.
  • 45
    • 0025886768 scopus 로고
    • Ligands 12b and 12c have not been tested in asymmetric hydrogenation
    • M.J. Burk, J.E. Feaster, R.L. Harlow, Tetrahedron; Asymm. 1991, 2, 569. Ligands 12b and 12c have not been tested in asymmetric hydrogenation.
    • (1991) Tetrahedron; Asymm. , vol.2 , pp. 569
    • Burk, M.J.1    Feaster, J.E.2    Harlow, R.L.3
  • 47
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    • see Ref.12
    • see Ref.12;
  • 72
    • 1842557260 scopus 로고    scopus 로고
    • Note added in proof: a new class ofmonodentate phosphites based on a combination of D-mannitol and BINOL or bisphenols affords excellent ee s in the hydrogenation of α-and β-α-acyl-dehydroamino esters, N-acyl enamides and itaconates, see:
    • Note added in proof: a new class ofmonodentate phosphites based on a combination of D-mannitol and BINOL or bisphenols affords excellent ee s in the hydrogenation of α-and β-α-acyl-dehydroamino esters, N-acyl enamides and itaconates, see: H. Huang, Z. Zheng, H. Luo, C. Bai, X. Hu, H. Chen, J. Org. Chem. 2004, 69, 2355.
    • (2004) J. Org. Chem. , vol.69 , pp. 2355
    • Huang, H.1    Zheng, Z.2    Luo, H.3    Bai, C.4    Hu, X.5    Chen, H.6
  • 76
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    • For alternative routes, see: (a) Ref.17
    • For alternative routes, see: (a) Ref.17;
  • 97
    • 84890981545 scopus 로고    scopus 로고
    • PhD. Thesis, University of Groningen, The Netherlands
    • M. van den Berg, PhD. Thesis 2005, University of Groningen, The Netherlands.
    • (2005)
    • Van Den Berg, M.1
  • 108
    • 84891003951 scopus 로고    scopus 로고
    • The methyl-substituted substrate has been hydrogenated with SIPHOS in excellent ee; see: Ref. [68b]
    • The methyl-substituted substrate has been hydrogenated with SIPHOS in excellent ee; see: Ref. [68b].
  • 109
    • 84890980202 scopus 로고    scopus 로고
    • MonoPhos 29a has shown to give the same ee-values for N-acyl, N-BOC and N-Z protection (unpublished results)
    • MonoPhos 29a has shown to give the same ee-values for N-acyl, N-BOC and N-Z protection (unpublished results).
  • 116
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    • r the enantioselective hydrogenation of cyclopenta-1, 3, 4, -trione using Rh/CAMP
    • J. Solodar, Chemtech 1975, 421. For the enantioselective hydrogenation of cyclopenta-1, 3, 4, -trione using Rh/CAMP
    • (1975) Chemtech , pp. 421
    • Solodar, J.1


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