메뉴 건너뛰기




Volumn 6, Issue , 2015, Pages

Dynamic control of chirality in phosphine ligands for enantioselective catalysis

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR MOTOR; PALLADIUM; PHOSPHINE;

EID: 84925808778     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms7652     Document Type: Article
Times cited : (164)

References (35)
  • 1
    • 84870894669 scopus 로고    scopus 로고
    • Catalytic chemical transformations with conformationally dynamic catalytic systems
    • Kumagai, N. & Shibasaki, M. Catalytic chemical transformations with conformationally dynamic catalytic systems. Catal. Sci. Technol. 3, 41-57 (2013).
    • (2013) Catal. Sci. Technol. , vol.3 , pp. 41-57
    • Kumagai, N.1    Shibasaki, M.2
  • 2
    • 77954839339 scopus 로고    scopus 로고
    • Artificial light-gated catalyst systems
    • Stoll, R. S. & Hecht, S. Artificial light-gated catalyst systems. Angew. Chem. Int. Ed. 49, 5054-5075 (2010).
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 5054-5075
    • Stoll, R.S.1    Hecht, S.2
  • 3
    • 84881274217 scopus 로고    scopus 로고
    • Illuminating photoswitchable catalysis
    • Neilson, B. M. & Bielawski, C. W. Illuminating photoswitchable catalysis. ACS Catal. 3, 1874-1885 (2013).
    • (2013) ACS Catal. , vol.3 , pp. 1874-1885
    • Neilson, B.M.1    Bielawski, C.W.2
  • 5
    • 84876917501 scopus 로고    scopus 로고
    • In situ manipulation of catalyst performance via the photocontrolled aggregation/dissociation state of the catalyst
    • Nojiri, A., Kumagai, N. & Shibasaki, M. In situ manipulation of catalyst performance via the photocontrolled aggregation/dissociation state of the catalyst. Chem. Commun. 49, 4628-4630 (2013).
    • (2013) Chem. Commun. , vol.49 , pp. 4628-4630
    • Nojiri, A.1    Kumagai, N.2    Shibasaki, M.3
  • 6
    • 77953305704 scopus 로고    scopus 로고
    • High-molecular-weight polyquinoxaline-based helically chiral phosphine (PQXphos) as chiralityswitchable, reusable, and highly enantioselective monodentate ligand in catalytic asymmetric hydrosilylation of styrenes
    • Yamamoto, T., Yamada, T., Nagata, Y. & Suginome, M. High-molecular-weight polyquinoxaline-based helically chiral phosphine (PQXphos) as chiralityswitchable, reusable, and highly enantioselective monodentate ligand in catalytic asymmetric hydrosilylation of styrenes. J. Am. Chem. Soc. 132, 7899-7901 (2010).
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 7899-7901
    • Yamamoto, T.1    Yamada, T.2    Nagata, Y.3    Suginome, M.4
  • 7
    • 79952799390 scopus 로고    scopus 로고
    • Dynamic control of chiral space in a catalytic asymmetric reaction using a molecular motor
    • Wang, J. & Feringa, B. L. Dynamic control of chiral space in a catalytic asymmetric reaction using a molecular motor. Science 331, 1429-1432 (2011).
    • (2011) Science , vol.331 , pp. 1429-1432
    • Wang, J.1    Feringa, B.L.2
  • 8
    • 84903204437 scopus 로고    scopus 로고
    • Dual stereocontrol over the Henry reaction using a light-and heat-triggered organocatalyst
    • Vlatković, M., Bernardi, L., Otten, E. & Feringa, B. L. Dual stereocontrol over the Henry reaction using a light-and heat-triggered organocatalyst. Chem. Commun. 50, 7773-7775 (2014).
    • (2014) Chem. Commun. , vol.50 , pp. 7773-7775
    • Vlatković, M.1    Bernardi, L.2    Otten, E.3    Feringa, B.L.4
  • 9
    • 84862095015 scopus 로고    scopus 로고
    • A redox-reconfigurable, ambidextrous asymmetric catalyst
    • Mortezaei, S., Catarineu, N. R. & Canary, J. W. A redox-reconfigurable, ambidextrous asymmetric catalyst. J. Am. Chem. Soc. 134, 8054-8057 (2012).
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 8054-8057
    • Mortezaei, S.1    Catarineu, N.R.2    Canary, J.W.3
  • 12
    • 77949627101 scopus 로고    scopus 로고
    • Unexpected inversions in asymmetric reactions: Reactions with chiral metal complexes, chiral organocatalysts, and heterogeneous chiral catalysts
    • Bartók, M. Unexpected inversions in asymmetric reactions: reactions with chiral metal complexes, chiral organocatalysts, and heterogeneous chiral catalysts. Chem. Rev. 110, 1663-1705 (2010).
    • (2010) Chem. Rev. , vol.110 , pp. 1663-1705
    • Bartók, M.1
  • 13
    • 84878636019 scopus 로고    scopus 로고
    • New advances in dual stereocontrol for asymmetric reactions
    • Escorihuela, J., Burguete, M. I. & Luis, S. V. New advances in dual stereocontrol for asymmetric reactions. Chem. Soc. Rev. 42, 5595-5617 (2013).
    • (2013) Chem. Soc. Rev. , vol.42 , pp. 5595-5617
    • Escorihuela, J.1    Burguete, M.I.2    Luis, S.V.3
  • 14
    • 0035840992 scopus 로고    scopus 로고
    • Switching enantiofacial selectivities using one chiral source: Catalytic enantioselective synthesis of the key intermediate for (20S)-camptothecin family by (S)-selective cyanosilylation of ketones
    • Yabu, K. et al. Switching enantiofacial selectivities using one chiral source: catalytic enantioselective synthesis of the key intermediate for (20S)-camptothecin family by (S)-selective cyanosilylation of ketones. J. Am. Chem. Soc. 123, 9908-9909 (2001).
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9908-9909
    • Yabu, K.1
  • 15
    • 78650084572 scopus 로고    scopus 로고
    • Asymmetric iron-catalysed hydrosilane reduction of ketones: Effect of zinc metal upon the absolute configuration
    • Inagaki, T., Ito, A., Ito, J. & Nishiyama, H. Asymmetric iron-catalysed hydrosilane reduction of ketones: effect of zinc metal upon the absolute configuration. Angew. Chem. Int. Ed. 49, 9384-9387 (2010).
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 9384-9387
    • Inagaki, T.1    Ito, A.2    Ito, J.3    Nishiyama, H.4
  • 16
    • 84555177970 scopus 로고    scopus 로고
    • Stereodivergency in catalytic asymmetric conjugate addition reactions of glycine (ket)imines
    • Kim, H., Li, J., Kim, S. & Oh, K. Stereodivergency in catalytic asymmetric conjugate addition reactions of glycine (ket)imines. J. Am. Chem. Soc. 133, 20750-20753 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 20750-20753
    • Kim, H.1    Li, J.2    Kim, S.3    Oh, K.4
  • 17
    • 1442276308 scopus 로고    scopus 로고
    • Enantioselective Friedel-Crafts reaction of indoles with arylidene malonates catalysed by iPr-bisoxazoline-Cu(OTf)
    • Zhou, J. & Tang, Y. Enantioselective Friedel-Crafts reaction of indoles with arylidene malonates catalysed by iPr-bisoxazoline-Cu(OTf)2. Chem. Commun. 432-433 (2004).
    • (2004) Chem. Commun. , vol.2 , pp. 432-433
    • Zhou, J.1    Tang, Y.2
  • 18
    • 0001158967 scopus 로고
    • An optical yield that increases with temperature in a photochemically induced enantiomeric isomerization
    • Inoue, Y., Yokoyama, T., Yamasaki, N. & Tai, A. An optical yield that increases with temperature in a photochemically induced enantiomeric isomerization. Nature 341, 225-226 (1989).
    • (1989) Nature , vol.341 , pp. 225-226
    • Inoue, Y.1    Yokoyama, T.2    Yamasaki, N.3    Tai, A.4
  • 19
    • 2342472565 scopus 로고    scopus 로고
    • Reversal of enantioselectivity in the hydroformylation of styrene with [2S, 4S-BDPP] Pt(SnCl3)Cl at high temperature arises from a change in the enantioselective-determining step
    • Casey, C. P., Martins, S. C. & Fagan, M. A. Reversal of enantioselectivity in the hydroformylation of styrene with [2S, 4S-BDPP]Pt(SnCl3)Cl at high temperature arises from a change in the enantioselective-determining step. J. Am. Chem. Soc. 126, 5585-5592 (2004).
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 5585-5592
    • Casey, C.P.1    Martins, S.C.2    Fagan, M.A.3
  • 20
    • 69949190011 scopus 로고    scopus 로고
    • Development of ruthenium catalysts for the enantioselective synthesis of P-stereogenic phosphines via nucleophilic phosphido intermediates
    • Chan, V. S., Chiu, M., Bergman, R. G. & Toste, F. D. Development of ruthenium catalysts for the enantioselective synthesis of P-stereogenic phosphines via nucleophilic phosphido intermediates. J. Am. Chem. Soc. 131, 6021-6032 (2009).
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 6021-6032
    • Chan, V.S.1    Chiu, M.2    Bergman, R.G.3    Toste, F.D.4
  • 22
    • 34548760154 scopus 로고    scopus 로고
    • The art of building small: From molecular switches to molecular motors
    • Feringa, B. L. The art of building small: from molecular switches to molecular motors. J. Org. Chem. 72, 6635-6652 (2007).
    • (2007) J. Org. Chem. , vol.72 , pp. 6635-6652
    • Feringa, B.L.1
  • 25
    • 38549098568 scopus 로고    scopus 로고
    • A redesign of light-driven rotary molecular motors
    • Pollard, M. M., Meetsma, A. & Feringa, B. L. A redesign of light-driven rotary molecular motors. Org. Biomol. Chem. 6, 507-512 (2008).
    • (2008) Org. Biomol. Chem. , vol.6 , pp. 507-512
    • Pollard, M.M.1    Meetsma, A.2    Feringa, B.L.3
  • 26
    • 0043240879 scopus 로고    scopus 로고
    • New chiral phosphorus ligands for enantioselective hydrogenation
    • Tang, W. J. & Zhang, X. M. New chiral phosphorus ligands for enantioselective hydrogenation. Chem. Rev. 103, 3029-3069 (2003).
    • (2003) Chem. Rev. , vol.103 , pp. 3029-3069
    • Tang, W.J.1    Zhang, X.M.2
  • 27
    • 84919683683 scopus 로고    scopus 로고
    • Photomechanical actuation of ligand geometry in enantioselective catalysis
    • Kean, Z. S. et al. Photomechanical actuation of ligand geometry in enantioselective catalysis. Angew. Chem. Int. Ed. 53, 14508-14511 (2014).
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 14508-14511
    • Kean, Z.S.1
  • 28
    • 1642324310 scopus 로고
    • A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalysed ionizations
    • Trost, B. M., Van Vranken, D. L. & Bingel, C. A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalysed ionizations. J. Am. Chem. Soc. 114, 9327-9343 (1992).
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9327-9343
    • Trost, B.M.1    Van Vranken, D.L.2    Bingel, C.3
  • 29
    • 0042379988 scopus 로고    scopus 로고
    • Asymmetric transition-metal-catalysed allylic alkylations: Applications in total synthesis
    • Trost, B. M. & Crawley, M. L. Asymmetric transition-metal-catalysed allylic alkylations: applications in total synthesis. Chem. Rev. 103, 2921-2944 (2003).
    • (2003) Chem. Rev. , vol.103 , pp. 2921-2944
    • Trost, B.M.1    Crawley, M.L.2
  • 30
    • 84906281149 scopus 로고    scopus 로고
    • Asymmetric synthesis of first generation molecular motors
    • Neubauer, T. M. et al. Asymmetric synthesis of first generation molecular motors. Org. Lett. 16, 4220-4223 (2014).
    • (2014) Org. Lett. , vol.16 , pp. 4220-4223
    • Neubauer, T.M.1
  • 31
    • 80052083175 scopus 로고    scopus 로고
    • Chiral Brønsted acid from a cationic gold(I) complex: Catalytic enantioselective protonation of silyl enol ethers of ketones
    • Cheon, C. H., Kanno, O. & Toste, F. D. Chiral Brønsted acid from a cationic gold(I) complex: catalytic enantioselective protonation of silyl enol ethers of ketones. J. Am. Chem. Soc. 133, 13248-13251 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 13248-13251
    • Cheon, C.H.1    Kanno, O.2    Toste, F.D.3
  • 33
    • 67651233273 scopus 로고    scopus 로고
    • Structure-based rationale for selectivity in the asymmetric allylic alkylation of cycloalkenyl esters employing the Trost'Standard Ligand' (TSL): Isolation, analysis and alkylation of the monomeric form of the cationic Z3-cyclohexenyl complex [(Z3-c-C6H9)Pd(TSL)]\+
    • Butts, C. P. et al. Structure-based rationale for selectivity in the asymmetric allylic alkylation of cycloalkenyl esters employing the Trost 'Standard Ligand' (TSL): isolation, analysis and alkylation of the monomeric form of the cationic Z3-cyclohexenyl complex [(Z3-c-C6H9)Pd(TSL)]\+. J. Am. Chem. Soc. 131, 9945-9957 (2009).
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 9945-9957
    • Butts, C.P.1
  • 34
    • 0000455625 scopus 로고    scopus 로고
    • Enhanced enantioselectivity in the desymmetrization of meso-biscarbamates
    • Trost, B. M. & Patterson, D. E. Enhanced enantioselectivity in the desymmetrization of meso-biscarbamates. J. Org. Chem 63, 1339-1341 (1998).
    • (1998) J. Org. Chem , vol.63 , pp. 1339-1341
    • Trost, B.M.1    Patterson, D.E.2
  • 35
    • 84925708886 scopus 로고
    • Reaction of sulfonyl isocyanates with polymeric alcohols to produce a polymeric acid
    • Taylor, L. D., Pluhar, M. & Rubin, L. E. Reaction of sulfonyl isocyanates with polymeric alcohols to produce a polymeric acid. J. Polym. Sci. B Polym. Lett. 5, 77-78 (1967).
    • (1967) J. Polym. Sci. B Polym. Lett. , vol.5 , pp. 77-78
    • Taylor, L.D.1    Pluhar, M.2    Rubin, L.E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.