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Volumn 111, Issue 3, 2011, Pages 2119-2176

Phosphine-phosphinite and phosphine-phosphite ligands: Preparation and applications in asymmetric catalysis

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC TRANSFORMATIONS; BIDENTATE PHOSPHINES; CHIRAL LIGAND; CHIRAL POOL; ENANTIOPURE; ENANTIOSELECTIVE CATALYSIS; EQUIMOLAR AMOUNT; PHOSPHINITES; PHOSPHITE LIGANDS; STARTING MATERIALS; SUPRAMOLECULAR COMPLEXES;

EID: 79952679097     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr100244e     Document Type: Review
Times cited : (368)

References (316)
  • 23
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    • Chiral Phosphine-Aminophosphines,-Phosphites,-Phosphonites,-Phosphinites, and Related P/N-Ligands
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    • Boaz, N. W.; Ponasik, J. A., Jr. Chiral Phosphine-Aminophosphines,- Phosphites,-Phosphonites,-Phosphinites, and Related P/N-Ligands. In Phosphorus Ligands in Asymmetric Catalysis; Börner, A., Ed.; Wiley-VCH: Weinheim, 2008; Vol. II, p 453.
    • (2008) Phosphorus Ligands in Asymmetric Catalysis , vol.2 , pp. 453
    • Boaz, N.W.1    Ponasik Jr., J.A.2    Börner, A.3
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    • See, for example, the following references and those cited therein
    • See, for example, the following references and those cited therein: Brunner, H.; Sicheneder, A. Angew. Chem., Int. Ed. Engl. 1988, 100, 718
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.100 , pp. 718
    • Brunner, H.1    Sicheneder, A.2
  • 51
    • 79952667953 scopus 로고    scopus 로고
    • Despite the absence of substituents on positions 6 and 6' of the biphenyl moiety in ligands 44b/44d, the latter were obtained as an inseparable 55:45 mixture of diastereomers (44b to 44d) rather than a single enantiomer (see ref 31)
    • Despite the absence of substituents on positions 6 and 6' of the biphenyl moiety in ligands 44b/44d, the latter were obtained as an inseparable 55:45 mixture of diastereomers (44b to 44d) rather than a single enantiomer (see ref 31).
  • 101
    • 79952672311 scopus 로고    scopus 로고
    • The two diastereoisomers arise from bonding the phosphite group to each of the two possible meta positions to the oxygens from the pyrocatechol unit
    • The two diastereoisomers arise from bonding the phosphite group to each of the two possible meta positions to the oxygens from the pyrocatechol unit.
  • 110
    • 79952642746 scopus 로고    scopus 로고
    • See, for example
    • See, for example
  • 133
    • 0000701744 scopus 로고    scopus 로고
    • Hydrogenation of Functionalized Carbon-Carbon Double Bonds
    • In;;;, Eds.; Springer-Verlag: Heidelberg,; Vols. I-III, p
    • Brown, J. M. Hydrogenation of Functionalized Carbon-Carbon Double Bonds In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vols. I-III, p 121.
    • (1999) Comprehensive Asymmetric Catalysis , pp. 121
    • Brown, J.M.1    Jacobsen, E.N.2    Pfaltz, A.3    Yamamoto, H.4
  • 134
    • 0000361977 scopus 로고    scopus 로고
    • Hydrogenation of Non-Functionalized Carbon-Carbon Double Bonds
    • In;;;, Eds.; Springer-Verlag: Heidelberg,; Vol. I, p
    • Halterman, R. L. Hydrogenation of Non-Functionalized Carbon-Carbon Double Bonds. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vol. I, p 183.
    • (1999) Comprehensive Asymmetric Catalysis , pp. 183
    • Halterman, R.L.1    Jacobsen, E.N.2    Pfaltz, A.3    Yamamoto, H.4
  • 181
    • 79952684419 scopus 로고    scopus 로고
    • Table 9 is not intended to provide a detailed comparison of the enantioselectivities obtained with P-OP ligands with those obtained with the many hundreds of efficient ligands that have been developed up until now for this transformation. Due to space limitations, the authors have considered only a very limited set of P-containing derivatives that, in their opinion, have played a key role in the development of the field and that allow comparison with the results reported for P-OP ligands. The reader is referred to more specific reviews on asymmetric hydrogenation for more detailed comparison with many kinds of highly efficient ligands (for example, see ref 61)
    • Table 9 is not intended to provide a detailed comparison of the enantioselectivities obtained with P-OP ligands with those obtained with the many hundreds of efficient ligands that have been developed up until now for this transformation. Due to space limitations, the authors have considered only a very limited set of P-containing derivatives that, in their opinion, have played a key role in the development of the field and that allow comparison with the results reported for P-OP ligands. The reader is referred to more specific reviews on asymmetric hydrogenation for more detailed comparison with many kinds of highly efficient ligands (for example, see ref 61).
  • 202
    • 79952649489 scopus 로고    scopus 로고
    • Although several examples of rhodium complexes of phosphine-phosphite ligands catalyzing enantioselective hydroformylations have been published, to the best of the author's knowledge, examples on the application of rhodium complexes of phosphine-phosphinites are very scarce in the literature. In this example, the ligand decomposed under the reaction conditions (22)
    • Although several examples of rhodium complexes of phosphine-phosphite ligands catalyzing enantioselective hydroformylations have been published, to the best of the author's knowledge, examples on the application of rhodium complexes of phosphine-phosphinites are very scarce in the literature. In this example, the ligand decomposed under the reaction conditions (22)
  • 228
    • 79952632370 scopus 로고
    • International Patent WO 9303839
    • Babin, J. E.; Whiteker, G. T. International Patent WO 9303839, 1993.
    • (1993)
    • Babin, J.E.1    Whiteker, G.T.2
  • 247
    • 79952638543 scopus 로고
    • US Patent 2,577,208
    • Reppe, W.; Magin, A. US Patent 2,577,208, 1951.
    • (1951)
    • Reppe, W.1    Magin, A.2
  • 248
    • 79952639823 scopus 로고    scopus 로고
    • Stereochemical considerations for the alternating copolymerization of CO and disubstituted or further substituted alkenes are not relevant, since alternating copolymerization with this kind of alkene hardly proceeds
    • Stereochemical considerations for the alternating copolymerization of CO and disubstituted or further substituted alkenes are not relevant, since alternating copolymerization with this kind of alkene hardly proceeds.
  • 259
    • 79952663476 scopus 로고    scopus 로고
    • The chain-terminating step was supposed to be the β-hydride elimination from an alkylpalladium species
    • The chain-terminating step was supposed to be the β-hydride elimination from an alkylpalladium species.
  • 282
    • 79952673305 scopus 로고    scopus 로고
    • The configuration of palladium complexes bearing an allyl ligand whose distal carbons are pointing in opposite direction to the substituents of the ligand backbone are referred to as exo; accordingly, when the allylic distal carbons point in the same direction as the ligand backbone substituents, the complex is described as endo
    • The configuration of palladium complexes bearing an allyl ligand whose distal carbons are pointing in opposite direction to the substituents of the ligand backbone are referred to as exo; accordingly, when the allylic distal carbons point in the same direction as the ligand backbone substituents, the complex is described as endo.
  • 284
    • 79952661750 scopus 로고    scopus 로고
    • Table 34 is not intended to provide a detailed comparison of the enantioselectivities obtained with P-OP ligands with those obtained with the many dozens of efficient ligands that have been developed up until now for this transformation. Due to space limitations, the authors have considered only the required set of ligands that allow comparison with the few results reported for P-OP ligands. The reader is referred to more specific reviews on allylic substitution for more detailed comparison with many kinds of highly efficient ligands (for example, see ref 152)
    • Table 34 is not intended to provide a detailed comparison of the enantioselectivities obtained with P-OP ligands with those obtained with the many dozens of efficient ligands that have been developed up until now for this transformation. Due to space limitations, the authors have considered only the required set of ligands that allow comparison with the few results reported for P-OP ligands. The reader is referred to more specific reviews on allylic substitution for more detailed comparison with many kinds of highly efficient ligands (for example, see ref 152).
  • 290
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    • See the following leading references, and references cited therein
    • See the following leading references, and references cited therein: Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957
    • (1997) Tetrahedron , vol.53 , pp. 4957
    • Beletskaya, I.1    Pelter, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.