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Volumn 11, Issue 9, 2000, Pages 1943-1955

Optically active palladacycles containing imines derived from 1-(1-naphthyl)ethylamine: new resolving agents for P-chiral phosphines

Author keywords

[No Author keywords available]

Indexed keywords

1 (1 NAPHTHYL) ETHYLAMINE; ORGANOMETALLIC COMPOUND; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0034686060     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00143-9     Document Type: Article
Times cited : (58)

References (63)
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    • (a) Barton, D.; Ollis, W. D., Eds.; Pergamon: Oxford Chapter 8
    • (a) Tennant, G. Comprehensive Organic Chemistry; Barton, D.; Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 2, Chapter 8.
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    • The destabilizing effect of two soft ligands in mutual trans positions has been called antisymbiosis, see: (a)
    • The destabilizing effect of two soft ligands in mutual trans positions has been called antisymbiosis, see: (a) Davies, J. A.; Hartley, F. R. Chem. Rev. 1981, 81, 79. (b) Pearson, R. G. Inorg. Chem. 1973, 12, 712. (c) Navarro, R.; Urriolabeitia, E. P. J. Chem. Soc., Dalton Trans. 1999, 4111. Recently, the term transphobia has been proposed to describe the difficulty of coordinating mutually trans phosphine and aryl ligands in paladium complexes, see: (d) Vicente, J.; Abad, J. A.; Frankland, A. D.; Ramírez De Arellano, M. C. Chem. Eur. J. 1999, 5, 3066. (e) Vicente, J.; Arcas, A.; Bautista, D.; Jones, P. G. Organometallics 1997, 16, 2127.
    • (1981) Chem. Rev. , vol.81 , pp. 79
    • Davies, J.A.1    Hartley, F.R.2
  • 47
    • 33845340540 scopus 로고
    • (b)
    • The destabilizing effect of two soft ligands in mutual trans positions has been called antisymbiosis, see: (a) Davies, J. A.; Hartley, F. R. Chem. Rev. 1981, 81, 79. (b) Pearson, R. G. Inorg. Chem. 1973, 12, 712. (c) Navarro, R.; Urriolabeitia, E. P. J. Chem. Soc., Dalton Trans. 1999, 4111. Recently, the term transphobia has been proposed to describe the difficulty of coordinating mutually trans phosphine and aryl ligands in paladium complexes, see: (d) Vicente, J.; Abad, J. A.; Frankland, A. D.; Ramírez de Arellano, M. C. Chem. Eur. J. 1999, 5, 3066. (e) Vicente, J.; Arcas, A.; Bautista, D.; Jones, P. G. Organometallics 1997, 16, 2127.
    • (1973) Inorg. Chem. , vol.12 , pp. 712
    • Pearson, R.G.1
  • 48
    • 33748810552 scopus 로고    scopus 로고
    • (c)
    • The destabilizing effect of two soft ligands in mutual trans positions has been called antisymbiosis, see: (a) Davies, J. A.; Hartley, F. R. Chem. Rev. 1981, 81, 79. (b) Pearson, R. G. Inorg. Chem. 1973, 12, 712. (c) Navarro, R.; Urriolabeitia, E. P. J. Chem. Soc., Dalton Trans. 1999, 4111. Recently, the term transphobia has been proposed to describe the difficulty of coordinating mutually trans phosphine and aryl ligands in paladium complexes, see: (d) Vicente, J.; Abad, J. A.; Frankland, A. D.; Ramírez de Arellano, M. C. Chem. Eur. J. 1999, 5, 3066. (e) Vicente, J.; Arcas, A.; Bautista, D.; Jones, P. G. Organometallics 1997, 16, 2127.
    • (1999) J. Chem. Soc., Dalton Trans. , pp. 4111
    • Navarro, R.1    Urriolabeitia, E.P.2
  • 49
    • 0032878804 scopus 로고    scopus 로고
    • Recently, the term transphobia has been proposed to describe the difficulty of coordinating mutually trans phosphine and aryl ligands in paladium complexes, see: (d)
    • The destabilizing effect of two soft ligands in mutual trans positions has been called antisymbiosis, see: (a) Davies, J. A.; Hartley, F. R. Chem. Rev. 1981, 81, 79. (b) Pearson, R. G. Inorg. Chem. 1973, 12, 712. (c) Navarro, R.; Urriolabeitia, E. P. J. Chem. Soc., Dalton Trans. 1999, 4111. Recently, the term transphobia has been proposed to describe the difficulty of coordinating mutually trans phosphine and aryl ligands in paladium complexes, see: (d) Vicente, J.; Abad, J. A.; Frankland, A. D.; Ramírez de Arellano, M. C. Chem. Eur. J. 1999, 5, 3066. (e) Vicente, J.; Arcas, A.; Bautista, D.; Jones, P. G. Organometallics 1997, 16, 2127.
    • (1999) Chem. Eur. J. , vol.5 , pp. 3066
    • Vicente, J.1    Abad, J.A.2    Frankland, A.D.3    Ramírez De Arellano, M.C.4
  • 50
    • 0000867198 scopus 로고    scopus 로고
    • (e)
    • The destabilizing effect of two soft ligands in mutual trans positions has been called antisymbiosis, see: (a) Davies, J. A.; Hartley, F. R. Chem. Rev. 1981, 81, 79. (b) Pearson, R. G. Inorg. Chem. 1973, 12, 712. (c) Navarro, R.; Urriolabeitia, E. P. J. Chem. Soc., Dalton Trans. 1999, 4111. Recently, the term transphobia has been proposed to describe the difficulty of coordinating mutually trans phosphine and aryl ligands in paladium complexes, see: (d) Vicente, J.; Abad, J. A.; Frankland, A. D.; Ramírez de Arellano, M. C. Chem. Eur. J. 1999, 5, 3066. (e) Vicente, J.; Arcas, A.; Bautista, D.; Jones, P. G. Organometallics 1997, 16, 2127.
    • (1997) Organometallics , vol.16 , pp. 2127
    • Vicente, J.1    Arcas, A.2    Bautista, D.3    Jones, P.G.4
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    • 4); see Ref. 5f
    • 4); see Ref. 5f.
  • 59
    • 0342808270 scopus 로고    scopus 로고
    • The imine cyclopalladated derivatives permit the separation in 85% yield of the corresponding diastereomers containing benzylcyclohexylphenylphosphine coordinated with a d.e. higher than 95%. In contrast, when optically active palladacycles containing primary or tertiary amines are used as resolving agents, the maximum yield reported for the resolution of this phosphine is 70%; see Ref. 5a
    • The imine cyclopalladated derivatives permit the separation in 85% yield of the corresponding diastereomers containing benzylcyclohexylphenylphosphine coordinated with a d.e. higher than 95%. In contrast, when optically active palladacycles containing primary or tertiary amines are used as resolving agents, the maximum yield reported for the resolution of this phosphine is 70%; see Ref. 5a.
  • 62


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