메뉴 건너뛰기




Volumn , Issue , 2005, Pages 89-103

Enantioselective Catalysis Using Sterically and Electronically Unsymmetrical Ligands

Author keywords

Allylic alkylation; Asymmetric catalysis; C2 symmetry; De symmetrization; Electronic differentiation; Heck reaction; Hydrogenations; Metal complexes; Modular design; P,N ligands; Respective control; Steric differentiation

Indexed keywords

ALKYLATION; ALLYLATION; CATALYSIS; ENANTIOSELECTIVITY; HYDROGENATION; METAL COMPLEXES; STEEL BEAMS AND GIRDERS; TRANSITION METALS;

EID: 84949985025     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/3527605746.ch7     Document Type: Chapter
Times cited : (4)

References (36)
  • 1
    • 37049133322 scopus 로고
    • The Preparation and Properties of Tris(triphenylphosphine) halogenorhodium(I) and some Reactions thereof including Catalytic Homogeneous Hydrogenation of Olefins and Acetylenes and their Derivatives
    • J. A. Osborne, F. J. Jardine, J. F. Young, G. Wilkinson, The Preparation and Properties of Tris(triphenylphosphine) halogenorhodium(I) and some Reactions thereof including Catalytic Homogeneous Hydrogenation of Olefins and Acetylenes and their Derivatives, J. Chem. Soc. A. 1966, 1711-1732.
    • (1966) J. Chem. Soc. A , pp. 1711-1732
    • Osborne, J.A.1    Jardine, F.J.2    Young, J.F.3    Wilkinson, G.4
  • 3
    • 33444462389 scopus 로고
    • Catalytic Asymmetric Hydrogenation employing a Soluble, Optically Active, Rhodium Complex
    • W. S. Knowles, M. J. Sabacky, Catalytic Asymmetric Hydrogenation employing a Soluble, Optically Active, Rhodium Complex, J. Chem. Soc., Chem. Commun. 1968, 1445-1446.
    • (1968) J. Chem. Soc., Chem. Commun , pp. 1445-1446
    • Knowles, W.S.1    Sabacky, M.J.2
  • 4
    • 33947089148 scopus 로고
    • Asymmetric Catalytic Reduction with Transition Metal Complexes. I. A Catalytic System of Rhodium(I) with (-)-2,3-O-Isopropylidene-2,3- dihydroxy-1,4-bis(diphenylphosphino)butane, a New Chiral Diphosphine
    • H. B. Kagan, T.-P. Dang, Asymmetric Catalytic Reduction with Transition Metal Complexes. I. A Catalytic System of Rhodium(I) with (-)-2,3-O-Isopropylidene-2,3- dihydroxy-1,4-bis(diphenylphosphino)butane, a New Chiral Diphosphine, J. Am. Chem. Soc. 1972, 94, 6429-6433.
    • (1972) J. Am. Chem. Soc , vol.94 , pp. 6429-6433
    • Kagan, H.B.1    Dang, T.-P.2
  • 5
    • 0002032726 scopus 로고
    • 2-Symmetry and Asymmetric Induction, Chem. Rev. 1989, 89, 1581-1590.
    • (1989) Chem. Rev , vol.89 , pp. 1581-1590
    • Whitesell, J.K.1
  • 6
    • 84941200773 scopus 로고
    • Chiral Ligands for Asymmetric Catalysis
    • J. D. Morrison), Academic Press, London
    • H. B. Kagan, Chiral Ligands for Asymmetric Catalysis, in Asymmetric Synthesis, Vol. 5 (Ed. J. D. Morrison), Academic Press, London, 1985, pp. 1-40.
    • (1985) Asymmetric Synthesis , vol.5 , pp. 1-40
    • Kagan, H.B.1
  • 7
    • 0032978066 scopus 로고    scopus 로고
    • From Corrin Chemistry to Asymmetric Catalysis-A Personal Account
    • A. Pfaltz, From Corrin Chemistry to Asymmetric Catalysis-A Personal Account, Synlett, 1999, 835-842.
    • (1999) Synlett , pp. 835-842
    • Pfaltz, A.1
  • 9
    • 33845559274 scopus 로고
    • Metal Complexes of Hemilabile Ligands
    • J. C. Jeffrey, T. B. Rauchfuss, Metal Complexes of Hemilabile Ligands, Inorg. Chem. 1979, 2658-2666.
    • (1979) Inorg. Chem. , pp. 2658-2666
    • Jeffrey, J.C.1    Rauchfuss, T.B.2
  • 10
    • 84987539502 scopus 로고
    • Design Concept for Developing Highly Efficient Chiral Bisphosphine Ligands in Rhodium-Catalysed Asymmetric Hydrogenations
    • K. Inoguchi, S. Sakuraba, K. Achiwa, Design Concept for Developing Highly Efficient Chiral Bisphosphine Ligands in Rhodium-Catalysed Asymmetric Hydrogenations, Synlett, 1992, 169-178.
    • (1992) Synlett , pp. 169-178
    • Inoguchi, K.1    Sakuraba, S.2    Achiwa, K.3
  • 11
    • 84941207091 scopus 로고
    • Asymmetric Catalytic Hydrogenation:Mechanism and Origin of Enantioselection
    • J. D. Morrison), Academic Press, London,
    • J. Halpern, Asymmetric Catalytic Hydrogenation:Mechanism and Origin of Enantioselection, in Asymmetric Synthesis, Vol. 5 (Ed. J. D. Morrison), Academic Press, London, 1985, pp. 41-69.
    • (1985) Asymmetric Synthesis , vol.5 , pp. 41-69
    • Halpern, J.1
  • 12
    • 84949991267 scopus 로고    scopus 로고
    • 2-coordinated alkene (cf. Scheme 3)
    • 2-coordinated alkene (cf. Scheme 3).
  • 13
    • 0001681707 scopus 로고    scopus 로고
    • A Technically Useful Catalyst for the Homogeneous Enantioselective Hydrogenation of N-Aryl Imines: A Case Study
    • (Ed. R. E. Maltz), Dekker, New York
    • F. Spindler, B. Pugin, H.-P. Jalett, H.-P. Buser, U. Pittelkow, H.-U Blaser, A Technically Useful Catalyst for the Homogeneous Enantioselective Hydrogenation of N-Aryl Imines: A Case Study, in Catalysis of Organic Reactions (Ed. R. E. Maltz), Dekker, New York, 1996, pp. 153-168.
    • (1996) Catalysis of Organic Reactions , pp. 153-168
    • Spindler, F.1    Pugin, B.2    Jalett, H.-P.3    Buser, H.-P.4    Pittelkow, U.5    Blaser, H.-U.6
  • 14
    • 84949980059 scopus 로고    scopus 로고
    • In general, Pd-catalyzed allylic substitutions with 'soft' nucleophiles involve nucleophilic attack directly on the allyl unit, on the opposite face to that occupied by the metal. This is contrasted with the situation for 'hard' nucleophiles where the initial attack occurs at the metal, with subsequent migration of the nucleophile to the allyl moiety-the addition to the allyl unit therefore occurring from the same face as the metal. Obviously, this has profound implications on the stereochemical outcome
    • In general, Pd-catalyzed allylic substitutions with 'soft' nucleophiles involve nucleophilic attack directly on the allyl unit, on the opposite face to that occupied by the metal. This is contrasted with the situation for 'hard' nucleophiles where the initial attack occurs at the metal, with subsequent migration of the nucleophile to the allyl moiety-the addition to the allyl unit therefore occurring from the same face as the metal. Obviously, this has profound implications on the stereochemical outcome.
  • 15
    • 0000687774 scopus 로고    scopus 로고
    • Allylic Substitution Reactions
    • E. N. Jacobson, A. Pfaltz, H. Yamamoto, Springer, Berlin
    • A. Pfaltz and M. Lautens, Allylic Substitution Reactions, in Comprehensive Asymmetric Catalysis, Vol. II (Eds. E. N. Jacobson, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 883-886.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 883-886
    • Pfaltz, A.1    Lautens, M.2
  • 16
    • 6844254916 scopus 로고    scopus 로고
    • Asymmetric Transition Metal-Catalysed Allylic Alkylations
    • B. M. Trost, D. L. Van Vranken, Asymmetric Transition Metal-Catalysed Allylic Alkylations, Chem. Rev. 1996, 96, 395-422.
    • (1996) Chem. Rev , vol.96 , pp. 395-422
    • Trost, B.M.1    Van Vranken, D.L.2
  • 17
    • 84949936736 scopus 로고    scopus 로고
    • [16] these higher-energy species generally do not play a rô le in the catalytic cycle, so they can be ignored in the mechanistic discussion
    • [16] these higher-energy species generally do not play a rô le in the catalytic cycle, so they can be ignored in the mechanistic discussion.
  • 18
    • 84949974588 scopus 로고    scopus 로고
    • 3- complex
    • 3- complex.
  • 20
    • 84949934758 scopus 로고    scopus 로고
    • [16] Nevertheless, in most cases, the interchange is rapid compared with the rate of nucleophilic attack and, therefore, the product outcome does not necessarily depend on the intermediate isomer ratio (Curtin-Hammett principle)
    • [16] Nevertheless, in most cases, the interchange is rapid compared with the rate of nucleophilic attack and, therefore, the product outcome does not necessarily depend on the intermediate isomer ratio (Curtin-Hammett principle).
  • 22
    • 33845282832 scopus 로고
    • 3-Allyl)palladium Complexes. A Carbon-13 Nuclear Magnetic Resonance Study
    • 3-Allyl)palladium Complexes. A Carbon-13 Nuclear Magnetic Resonance Study, Organometallics, 1987, 6, 620-628.
    • (1987) Organometallics , vol.6 , pp. 620-628
    • Åkermark, B.1    Krakenberger, B.2    Hansson, S.3
  • 24
    • 0006989799 scopus 로고    scopus 로고
    • Enantioselective Catalysis with Complexes of Asymmetric P,N-Ligands
    • G. Helmchen, S. Kudis, H. Steinhagen, Enantioselective Catalysis with Complexes of Asymmetric P,N-Ligands, Pure & Appl. Chem. 1997, 69, 513-518.
    • (1997) Pure & Appl. Chem , vol.69 , pp. 513-518
    • Helmchen, G.1    Kudis, S.2    Steinhagen, H.3
  • 25
    • 0000273585 scopus 로고    scopus 로고
    • The Ups and Downs of Allylpalladium Complexes in Catalysis
    • J. M. J. Williams, The Ups and Downs of Allylpalladium Complexes in Catalysis, Synlett, 1996, 705-710.
    • (1996) Synlett , pp. 705-710
    • Williams, J.M.J.1
  • 26
    • 0028232428 scopus 로고
    • Mechanistic and Synthetic Studies in Catalytic Allylic Alkylation with Palladium Complexes of 1-(2-Diphenylphosphino-1-naphthyl)isoquinoline
    • J. M. Brown, D. I. Hulmes, P. J. Guiry, Mechanistic and Synthetic Studies in Catalytic Allylic Alkylation with Palladium Complexes of 1-(2-Diphenylphosphino-1-naphthyl)isoquinoline, Tetrahedron, 1994, 50, 4493-4506.
    • (1994) Tetrahedron , vol.50 , pp. 4493-4506
    • Brown, J.M.1    Hulmes, D.I.2    Guiry, P.J.3
  • 27
    • 0033949478 scopus 로고    scopus 로고
    • Phosphinooxazolines-A New Class of Versatile, Modular P,N-Ligands for Asymmetric Catalysis
    • G. Helmchen, A. Pfaltz, Phosphinooxazolines-A New Class of Versatile, Modular P,N-Ligands for Asymmetric Catalysis, Acc. Chem. Res. 2000, 33, 336-345.
    • (2000) Acc. Chem. Res , vol.33 , pp. 336-345
    • Helmchen, G.1    Pfaltz, A.2
  • 28
    • 0032731880 scopus 로고    scopus 로고
    • Chiral Bis(N-tosylamino)phosphineand TADDOL-Phosphite-Oxazolines as Ligands in Asymmetric Catalysis
    • R. Hilgraf, A. Pfaltz, Chiral Bis(N-tosylamino)phosphineand TADDOL-Phosphite-Oxazolines as Ligands in Asymmetric Catalysis, Synlett, 1999, 11, 1814-1816.
    • (1999) Synlett , vol.11 , pp. 1814-1816
    • Hilgraf, R.1    Pfaltz, A.2
  • 29
    • 17544398247 scopus 로고    scopus 로고
    • Phosphine-Pyridyl and Related Ligands in Synthesis and Catalysis
    • P. Espinet, K. Soulantica, Phosphine-Pyridyl and Related Ligands in Synthesis and Catalysis, Coord. Chem. Rev. 1999, 195, 499-556.
    • (1999) Coord. Chem. Rev , vol.195 , pp. 499-556
    • Espinet, P.1    Soulantica, K.2
  • 30
    • 0000361977 scopus 로고    scopus 로고
    • Hydrogenation of Non-Functionalised Carbon-Carbon Double Bonds
    • E. N. Jacobson, A. Pfaltz, H. Yamamoto, Springer, Berlin
    • R. L. Halterman, Hydrogenation of Non-Functionalised Carbon-Carbon Double Bonds, in Comprehensive Asymmetric Catalysis, Vol. I (Eds. E. N. Jacobson, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 183-189.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 183-189
    • Halterman, R.L.1
  • 31
    • 33845560987 scopus 로고
    • Iridium Compounds in Catalysis
    • R. Crabtree, Iridium Compounds in Catalysis, Acc. Chem. Res. 1979, 12, 331-337.
    • (1979) Acc. Chem. Res , vol.12 , pp. 331-337
    • Crabtree, R.1
  • 32
    • 0032476793 scopus 로고    scopus 로고
    • Enantioselective Hydrogenation of Olefins with Iridium-Phosphanophanodihydrooxazole Catalysts
    • A. Lightfoot, P. Schnider, A. Pfaltz, Enantioselective Hydrogenation of Olefins with Iridium-Phosphanophanodihydrooxazole Catalysts, Angew. Chem. Int. Ed. 1998, 37, 2897-2899.
    • (1998) Angew. Chem. Int. Ed , vol.37 , pp. 2897-2899
    • Lightfoot, A.1    Schnider, P.2    Pfaltz, A.3
  • 33
    • 0030944755 scopus 로고    scopus 로고
    • Enantioselective Hydrogenation of Imines with Chiral (Phospanodihydrooxazole)iridium Catalysts
    • P. Schnider, G. Koch, R. Pŕetot, G.Wang, F. M. Bohnen, C. Krüger, A. Pfaltz, Enantioselective Hydrogenation of Imines with Chiral (Phospanodihydrooxazole)iridium Catalysts, Chem. Eur. J. 1997, 3, 887-892.
    • (1997) Chem. Eur. J , vol.3 , pp. 887-892
    • Schnider, P.1    Koch, G.2    Pŕetot, R.3    Wang, G.4    Bohnen, F.M.5    Krüger, C.6    Pfaltz, A.7
  • 35
    • 0028272213 scopus 로고
    • Chiral Mercaptoaryl-oxazolines as Ligands in Enantioselective Copper-Catalyzed 1,4-Additions of Grignard Reagents to Enones
    • Q.-L. Zhou, A. Pfaltz, Chiral Mercaptoaryl-oxazolines as Ligands in Enantioselective Copper-Catalyzed 1,4-Additions of Grignard Reagents to Enones, Tetrahedron, 1994, 50, 4467-4478.
    • (1994) Tetrahedron , vol.50 , pp. 4467-4478
    • Zhou, Q.-L.1    Pfaltz, A.2
  • 36
    • 0033606284 scopus 로고    scopus 로고
    • Asymmetric Hydrogenation of Unfunctionalised Tetrasubstituted Olefins with a Cationic Zirconocene Catalyst
    • M. V. Troutman, D. H. Appella, S. L. Buchwald, Asymmetric Hydrogenation of Unfunctionalised Tetrasubstituted Olefins with a Cationic Zirconocene Catalyst, J. Am. Chem. Soc. 1999, 121, 4916-4917.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 4916-4917
    • Troutman, M.V.1    Appella, D.H.2    Buchwald, S.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.