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Volumn 624, Issue 1-2, 2001, Pages 271-286

Chiral platinum and palladium complexes containing functionalized C2-symmetric bisaminoaryl 'Pincer' ligands

Author keywords

Asymmetric synthesis; Homogeneous catalysis; Ligand tuning; Pincer N ligand; Platinum

Indexed keywords


EID: 0000077915     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(01)00667-2     Document Type: Article
Times cited : (108)

References (117)
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    • Notably, mesylation is fast and requires low temperatures to retain the optical purity, since these conditions successfully prevented nucleophilic substitution of the mesylate by residual chloride ions and subsequent racemization, see e.g. (a) W.T.S. Huck, F.C.J.M. van Veggel, D.N. Reinhoudt, J. Mater. Chem. 7 (1997) 1213. (b) P.J. Davies, D.M. Grove, G. van Koten, Organometallics 16 (1997) 800.
    • (1997) Organometallics , vol.16 , pp. 800
    • Davies, P.J.1    Grove, D.M.2    Van Koten, G.3
  • 70
    • 33748231234 scopus 로고
    • (b) P. Wijkens, E.M. van Koten, M.D. Janssen, J.T.B.H. Jastrzebski, A.L. Spek, G. van Koten, Angew. Chem. 107 (1995) 239; Angew. Chem. Int. Ed. Engl. 34 (1995) 219.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 219
  • 75
    • 0347800838 scopus 로고    scopus 로고
    • note
    • 3)N], see Ref. [30].
  • 76
    • 0347800839 scopus 로고    scopus 로고
    • note
    • Due to the puckered metallacycles, the R,S- and the S,R-isomers may be distinguished, since they are enantiotopic to each other. The term meso is therefore misleading and has been avoided for the description of the configuration of square-planar metal complexes (but not of ligand precursors). Only when the wagging of the metallacycles is fast, the meso-isomer is observed as an averaged structure. (Equation Presented)
  • 77
    • 0001103628 scopus 로고    scopus 로고
    • For pincer complexes on heterogeneous supports, see: (a) C. Pathmamanoharan, P. Wijkens, D.M. Grove, A.P. Philipse, Langmuir 12 (1996) 4372. For recent achievements in dendrimer chemistry, see: (b) G. van Koten, J.T.B.H. Jastrzebski, J. Mol Catal. A: Chem. 146 (1999) 317.
    • (1996) Langmuir , vol.12 , pp. 4372
    • Pathmamanoharan, C.1    Wijkens, P.2    Grove, D.M.3    Philipse, A.P.4
  • 78
    • 0033589328 scopus 로고    scopus 로고
    • For pincer complexes on heterogeneous supports, see: (a) C. Pathmamanoharan, P. Wijkens, D.M. Grove, A.P. Philipse, Langmuir 12 (1996) 4372. For recent achievements in dendrimer chemistry, see: (b) G. van Koten, J.T.B.H. Jastrzebski, J. Mol Catal. A: Chem. 146 (1999) 317.
    • (1999) J. Mol Catal. A: Chem. , vol.146 , pp. 317
    • Van Koten, G.1    Jastrzebski, J.T.B.H.2
  • 80
    • 0033152039 scopus 로고    scopus 로고
    • (c) N.J. Hovestad, E.B. Eggeling, H.J. Heidbüchel, J.T.B.H. Jastrzebski, U. Kragl, W. Keim, D. Vogt, G. van Koten, Angew. Chem. 111 (1999) 1763; Angew. Chem. Int. Ed. Engl. 38 (1999) 1655.
    • (1999) Angew. Chem. Int. Ed. Engl. , vol.38 , pp. 1655
  • 86
    • 0029961915 scopus 로고    scopus 로고
    • (b) P.J. Davies, N. Veldman, D.M. Grove, A.L. Spek, B.T.G. Lutz, G. van Koten, Angew. Chem. 108 (1996) 2078; Angew. Chem. Int. Ed. Engl. 35 (1996) 1959.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1959
  • 87
    • 0002233116 scopus 로고
    • This reaction requires an organolithium reagent and does not proceed well with the corresponding organomagnesium reagents, see: (a) M.J. Jorgenson, Org. React. 18 (1970) 1. (b) G.M. Rubottom, C.-W. Kim, J. Org. Chem. 48 (1983) 1550.
    • (1970) Org. React. , vol.18 , pp. 1
    • Jorgenson, M.J.1
  • 88
    • 0001642794 scopus 로고
    • This reaction requires an organolithium reagent and does not proceed well with the corresponding organomagnesium reagents, see: (a) M.J. Jorgenson, Org. React. 18 (1970) 1. (b) G.M. Rubottom, C.-W. Kim, J. Org. Chem. 48 (1983) 1550.
    • (1983) J. Org. Chem. , vol.48 , pp. 1550
    • Rubottom, G.M.1    Kim, C.-W.2
  • 90
    • 0347800834 scopus 로고    scopus 로고
    • The term ortho,ortho denotes the position ortho to both nitrogen-containing substituents of the arene, whereas ortho,ortho′ is referred to as the position ortho to two different substituents, i.e. ortho to the oxo-substituent and to one nitrogen-containing substituent
    • The term ortho,ortho denotes the position ortho to both nitrogen-containing substituents of the arene, whereas ortho,ortho′ is referred to as the position ortho to two different substituents, i.e. ortho to the oxo-substituent and to one nitrogen-containing substituent
  • 100
    • 0346540559 scopus 로고    scopus 로고
    • note
    • 2O quenches revealed 60-80% product resulting from retro-[1,2]-Brook rearrangement, dependent on whether n-BuLi or t-BuLi was used.
  • 103
    • 0347800830 scopus 로고    scopus 로고
    • note
    • Notably, reduction of the brominated ketone 12 (available from oxidation of rac/meso-11 by pyridinium chlorochromate) afforded the diol R,R-11 in higher optical purity (typically 94-97% of the desired stereoisomer) than reduction of the non-brominated analog R,R-6a (typically 90%). Presumably, the steric demand of the bromide substituent positively influences the crucial intermediates during the CBS reduction.
  • 111
    • 0034596926 scopus 로고    scopus 로고
    • C. Schlenk, A.W. Kleij, H. Frey, G. van Koten, Angew. Chem. 112 (2000) 3587; Angew. Chem. Int. Ed. Engl. 39 (2000) 3445.
    • (2000) Angew. Chem. Int. Ed. Engl. , vol.39 , pp. 3445


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