Enantiomer-selective activation of racemic catalysts

Accounts of Chemical Research

Volumn 33, Issue 6, 2000, Pages 391-401

  Mikami, Koichi ^a   Terada, Masahiro ^a   Korenaga, Toshinobu ^a   Matsumoto, Yousuke ^a   Matsukawa, Satoru ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HEAVY METAL; ORGANOMETALLIC COMPOUND; POLYCYCLIC HYDROCARBON;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL INTERACTION; CHEMISTRY; CHIRALITY; CONFORMATION; ENANTIOMER; HYDROGENATION; KINETICS; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STOICHIOMETRY; SYNTHESIS;

CATALYSIS; KINETICS; METALS, HEAVY; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; POLYCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 0033921495     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar9900818     Document Type: Article

References (105)

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90. 5-Phosphaphenanthren. Chem. Ber. 1982, 115, 1367-1373. For "BIPHEMP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethyl-1,1′-biphenyl), see: Svensson, G.; Albertsson, J.; Frejd, T.; Klingstedt, T. [(+)-(R)-2,2′-Bis(diphenylphosphino)-6,6′-dimethylbiphenyl](8,9,10- trinorborna-2,5-diene)rhodium(I) Tetrafluoroborate. Acta Crystallogr., Sect. C 1986, 42, 1324-1327. Schmid, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hansen, H.-J. Axially Dissymmetric Bis(triary)phosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine) ('BIPHEMP') and Analogues, and their Use in Rh-(I)-Catalyzed Asymmetric Isomerization of N,N-Diethylnerylamine. Helv. Chim. Acta 1988, 71, 897-929. For "BICHEPs" (2,2′-bis-(dicyclohexylphosphanyl)-6,6′-dimethyl-1,1′- biphenyl), see: Chiba, T.; Miyashita, A.; Nohira, H. Synthesis of Chiral Rh-BICHEP Complexes, Highly Efficient Catalysts for Asymmetric Hydrogenations. Tetrahedron Lett. 1991, 32, 4745-4748. For "MeO-BIPHEP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethoxy-1,1′-biphenyl), see: Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Axially Disymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)-('MeO- BIPHEP') and Analogues via an ortho-Lithiation/Iodination Ullmann-Reaction Approach. Helv. Chim. Acta 1991, 74, 370-389. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. New developments in enantioselective hydrogenation. Pure Appl. Chem. 1996, 68, 131-138. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. Enantioselective Homogeneous Catalysis and the "3,5-Dialkyl Meta-Effect". MeO-BIPHEP Complexes Related to Heck, Allylic Alkylation, and Hydrogenation Chemistry. J. Am. Chem. Soc. 1997, 119, 6315-6323. For 2,2′-bis(diphenylphosphanyl)-6,6′-difluoro-1,1′-biphenyl, see: Jendralla, H.; Li, C.-H.; Paulus, E. Efficient Synthesis of (R)- and (S)-(6,6′-Difluorobiphenyl-2,2′-diyl)bis(diphenylphosphine); Electron-Poor Biphenyl-Type Ligands for Transition Metal Catalysts. Tetrahedron: Asymmetry 1994, 5, 1297-1320.
91. 5-Phosphaphenanthren. Chem. Ber. 1982, 115, 1367-1373. For "BIPHEMP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethyl-1,1′-biphenyl), see: Svensson, G.; Albertsson, J.; Frejd, T.; Klingstedt, T. [(+)-(R)-2,2′-Bis(diphenylphosphino)-6,6′-dimethylbiphenyl](8,9,10- trinorborna-2,5-diene)rhodium(I) Tetrafluoroborate. Acta Crystallogr., Sect. C 1986, 42, 1324-1327. Schmid, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hansen, H.-J. Axially Dissymmetric Bis(triary)phosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine) ('BIPHEMP') and Analogues, and their Use in Rh-(I)-Catalyzed Asymmetric Isomerization of N,N-Diethylnerylamine. Helv. Chim. Acta 1988, 71, 897-929. For "BICHEPs" (2,2′-bis-(dicyclohexylphosphanyl)-6,6′-dimethyl-1,1′- biphenyl), see: Chiba, T.; Miyashita, A.; Nohira, H. Synthesis of Chiral Rh-BICHEP Complexes, Highly Efficient Catalysts for Asymmetric Hydrogenations. Tetrahedron Lett. 1991, 32, 4745-4748. For "MeO-BIPHEP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethoxy-1,1′-biphenyl), see: Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Axially Disymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)-('MeO- BIPHEP') and Analogues via an ortho-Lithiation/Iodination Ullmann-Reaction Approach. Helv. Chim. Acta 1991, 74, 370-389. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. New developments in enantioselective hydrogenation. Pure Appl. Chem. 1996, 68, 131-138. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. Enantioselective Homogeneous Catalysis and the "3,5-Dialkyl Meta-Effect". MeO-BIPHEP Complexes Related to Heck, Allylic Alkylation, and Hydrogenation Chemistry. J. Am. Chem. Soc. 1997, 119, 6315-6323. For 2,2′-bis(diphenylphosphanyl)-6,6′-difluoro-1,1′-biphenyl, see: Jendralla, H.; Li, C.-H.; Paulus, E. Efficient Synthesis of (R)- and (S)-(6,6′-Difluorobiphenyl-2,2′-diyl)bis(diphenylphosphine); Electron-Poor Biphenyl-Type Ligands for Transition Metal Catalysts. Tetrahedron: Asymmetry 1994, 5, 1297-1320.
92. 5-Phosphaphenanthren. Chem. Ber. 1982, 115, 1367-1373. For "BIPHEMP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethyl-1,1′-biphenyl), see: Svensson, G.; Albertsson, J.; Frejd, T.; Klingstedt, T. [(+)-(R)-2,2′-Bis(diphenylphosphino)-6,6′-dimethylbiphenyl](8,9,10- trinorborna-2,5-diene)rhodium(I) Tetrafluoroborate. Acta Crystallogr., Sect. C 1986, 42, 1324-1327. Schmid, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hansen, H.-J. Axially Dissymmetric Bis(triary)phosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine) ('BIPHEMP') and Analogues, and their Use in Rh-(I)-Catalyzed Asymmetric Isomerization of N,N-Diethylnerylamine. Helv. Chim. Acta 1988, 71, 897-929. For "BICHEPs" (2,2′-bis-(dicyclohexylphosphanyl)-6,6′-dimethyl-1,1′- biphenyl), see: Chiba, T.; Miyashita, A.; Nohira, H. Synthesis of Chiral Rh-BICHEP Complexes, Highly Efficient Catalysts for Asymmetric Hydrogenations. Tetrahedron Lett. 1991, 32, 4745-4748. For "MeO-BIPHEP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethoxy-1,1′-biphenyl), see: Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Axially Disymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)-('MeO- BIPHEP') and Analogues via an ortho-Lithiation/Iodination Ullmann-Reaction Approach. Helv. Chim. Acta 1991, 74, 370-389. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. New developments in enantioselective hydrogenation. Pure Appl. Chem. 1996, 68, 131-138. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. Enantioselective Homogeneous Catalysis and the "3,5-Dialkyl Meta-Effect". MeO-BIPHEP Complexes Related to Heck, Allylic Alkylation, and Hydrogenation Chemistry. J. Am. Chem. Soc. 1997, 119, 6315-6323. For 2,2′-bis(diphenylphosphanyl)-6,6′-difluoro-1,1′-biphenyl, see: Jendralla, H.; Li, C.-H.; Paulus, E. Efficient Synthesis of (R)- and (S)-(6,6′-Difluorobiphenyl-2,2′-diyl)bis(diphenylphosphine); Electron-Poor Biphenyl-Type Ligands for Transition Metal Catalysts. Tetrahedron: Asymmetry 1994, 5, 1297-1320.
93. 5-Phosphaphenanthren. Chem. Ber. 1982, 115, 1367-1373. For "BIPHEMP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethyl-1,1′-biphenyl), see: Svensson, G.; Albertsson, J.; Frejd, T.; Klingstedt, T. [(+)-(R)-2,2′-Bis(diphenylphosphino)-6,6′-dimethylbiphenyl](8,9,10- trinorborna-2,5-diene)rhodium(I) Tetrafluoroborate. Acta Crystallogr., Sect. C 1986, 42, 1324-1327. Schmid, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hansen, H.-J. Axially Dissymmetric Bis(triary)phosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine) ('BIPHEMP') and Analogues, and their Use in Rh-(I)-Catalyzed Asymmetric Isomerization of N,N-Diethylnerylamine. Helv. Chim. Acta 1988, 71, 897-929. For "BICHEPs" (2,2′-bis-(dicyclohexylphosphanyl)-6,6′-dimethyl-1,1′- biphenyl), see: Chiba, T.; Miyashita, A.; Nohira, H. Synthesis of Chiral Rh-BICHEP Complexes, Highly Efficient Catalysts for Asymmetric Hydrogenations. Tetrahedron Lett. 1991, 32, 4745-4748. For "MeO-BIPHEP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethoxy-1,1′-biphenyl), see: Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Axially Disymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)-('MeO- BIPHEP') and Analogues via an ortho-Lithiation/Iodination Ullmann-Reaction Approach. Helv. Chim. Acta 1991, 74, 370-389. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. New developments in enantioselective hydrogenation. Pure Appl. Chem. 1996, 68, 131-138. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. Enantioselective Homogeneous Catalysis and the "3,5-Dialkyl Meta-Effect". MeO-BIPHEP Complexes Related to Heck, Allylic Alkylation, and Hydrogenation Chemistry. J. Am. Chem. Soc. 1997, 119, 6315-6323. For 2,2′-bis(diphenylphosphanyl)-6,6′-difluoro-1,1′-biphenyl, see: Jendralla, H.; Li, C.-H.; Paulus, E. Efficient Synthesis of (R)- and (S)-(6,6′-Difluorobiphenyl-2,2′-diyl)bis(diphenylphosphine); Electron-Poor Biphenyl-Type Ligands for Transition Metal Catalysts. Tetrahedron: Asymmetry 1994, 5, 1297-1320.
94. 5-Phosphaphenanthren. Chem. Ber. 1982, 115, 1367-1373. For "BIPHEMP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethyl-1,1′-biphenyl), see: Svensson, G.; Albertsson, J.; Frejd, T.; Klingstedt, T. [(+)-(R)-2,2′-Bis(diphenylphosphino)-6,6′-dimethylbiphenyl](8,9,10- trinorborna-2,5-diene)rhodium(I) Tetrafluoroborate. Acta Crystallogr., Sect. C 1986, 42, 1324-1327. Schmid, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hansen, H.-J. Axially Dissymmetric Bis(triary)phosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine) ('BIPHEMP') and Analogues, and their Use in Rh-(I)-Catalyzed Asymmetric Isomerization of N,N-Diethylnerylamine. Helv. Chim. Acta 1988, 71, 897-929. For "BICHEPs" (2,2′-bis-(dicyclohexylphosphanyl)-6,6′-dimethyl-1,1′- biphenyl), see: Chiba, T.; Miyashita, A.; Nohira, H. Synthesis of Chiral Rh-BICHEP Complexes, Highly Efficient Catalysts for Asymmetric Hydrogenations. Tetrahedron Lett. 1991, 32, 4745-4748. For "MeO-BIPHEP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethoxy-1,1′-biphenyl), see: Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Axially Disymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)-('MeO- BIPHEP') and Analogues via an ortho-Lithiation/Iodination Ullmann-Reaction Approach. Helv. Chim. Acta 1991, 74, 370-389. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. New developments in enantioselective hydrogenation. Pure Appl. Chem. 1996, 68, 131-138. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. Enantioselective Homogeneous Catalysis and the "3,5-Dialkyl Meta-Effect". MeO-BIPHEP Complexes Related to Heck, Allylic Alkylation, and Hydrogenation Chemistry. J. Am. Chem. Soc. 1997, 119, 6315-6323. For 2,2′-bis(diphenylphosphanyl)-6,6′-difluoro-1,1′-biphenyl, see: Jendralla, H.; Li, C.-H.; Paulus, E. Efficient Synthesis of (R)- and (S)-(6,6′-Difluorobiphenyl-2,2′-diyl)bis(diphenylphosphine); Electron-Poor Biphenyl-Type Ligands for Transition Metal Catalysts. Tetrahedron: Asymmetry 1994, 5, 1297-1320.
95. 5-Phosphaphenanthren. Chem. Ber. 1982, 115, 1367-1373. For "BIPHEMP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethyl-1,1′-biphenyl), see: Svensson, G.; Albertsson, J.; Frejd, T.; Klingstedt, T. [(+)-(R)-2,2′-Bis(diphenylphosphino)-6,6′-dimethylbiphenyl](8,9,10- trinorborna-2,5-diene)rhodium(I) Tetrafluoroborate. Acta Crystallogr., Sect. C 1986, 42, 1324-1327. Schmid, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hansen, H.-J. Axially Dissymmetric Bis(triary)phosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine) ('BIPHEMP') and Analogues, and their Use in Rh-(I)-Catalyzed Asymmetric Isomerization of N,N-Diethylnerylamine. Helv. Chim. Acta 1988, 71, 897-929. For "BICHEPs" (2,2′-bis-(dicyclohexylphosphanyl)-6,6′-dimethyl-1,1′- biphenyl), see: Chiba, T.; Miyashita, A.; Nohira, H. Synthesis of Chiral Rh-BICHEP Complexes, Highly Efficient Catalysts for Asymmetric Hydrogenations. Tetrahedron Lett. 1991, 32, 4745-4748. For "MeO-BIPHEP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethoxy-1,1′-biphenyl), see: Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Axially Disymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)-('MeO- BIPHEP') and Analogues via an ortho-Lithiation/Iodination Ullmann-Reaction Approach. Helv. Chim. Acta 1991, 74, 370-389. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. New developments in enantioselective hydrogenation. Pure Appl. Chem. 1996, 68, 131-138. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. Enantioselective Homogeneous Catalysis and the "3,5-Dialkyl Meta-Effect". MeO-BIPHEP Complexes Related to Heck, Allylic Alkylation, and Hydrogenation Chemistry. J. Am. Chem. Soc. 1997, 119, 6315-6323. For 2,2′-bis(diphenylphosphanyl)-6,6′-difluoro-1,1′-biphenyl, see: Jendralla, H.; Li, C.-H.; Paulus, E. Efficient Synthesis of (R)- and (S)-(6,6′-Difluorobiphenyl-2,2′-diyl)bis(diphenylphosphine); Electron-Poor Biphenyl-Type Ligands for Transition Metal Catalysts. Tetrahedron: Asymmetry 1994, 5, 1297-1320.
96. 5-Phosphaphenanthren. Chem. Ber. 1982, 115, 1367-1373. For "BIPHEMP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethyl-1,1′-biphenyl), see: Svensson, G.; Albertsson, J.; Frejd, T.; Klingstedt, T. [(+)-(R)-2,2′-Bis(diphenylphosphino)-6,6′-dimethylbiphenyl](8,9,10- trinorborna-2,5-diene)rhodium(I) Tetrafluoroborate. Acta Crystallogr., Sect. C 1986, 42, 1324-1327. Schmid, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hansen, H.-J. Axially Dissymmetric Bis(triary)phosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine) ('BIPHEMP') and Analogues, and their Use in Rh-(I)-Catalyzed Asymmetric Isomerization of N,N-Diethylnerylamine. Helv. Chim. Acta 1988, 71, 897-929. For "BICHEPs" (2,2′-bis-(dicyclohexylphosphanyl)-6,6′-dimethyl-1,1′- biphenyl), see: Chiba, T.; Miyashita, A.; Nohira, H. Synthesis of Chiral Rh-BICHEP Complexes, Highly Efficient Catalysts for Asymmetric Hydrogenations. Tetrahedron Lett. 1991, 32, 4745-4748. For "MeO-BIPHEP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethoxy-1,1′-biphenyl), see: Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Axially Disymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)-('MeO- BIPHEP') and Analogues via an ortho-Lithiation/Iodination Ullmann-Reaction Approach. Helv. Chim. Acta 1991, 74, 370-389. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. New developments in enantioselective hydrogenation. Pure Appl. Chem. 1996, 68, 131-138. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. Enantioselective Homogeneous Catalysis and the "3,5-Dialkyl Meta-Effect". MeO-BIPHEP Complexes Related to Heck, Allylic Alkylation, and Hydrogenation Chemistry. J. Am. Chem. Soc. 1997, 119, 6315-6323. For 2,2′-bis(diphenylphosphanyl)-6,6′-difluoro-1,1′-biphenyl, see: Jendralla, H.; Li, C.-H.; Paulus, E. Efficient Synthesis of (R)- and (S)-(6,6′-Difluorobiphenyl-2,2′-diyl)bis(diphenylphosphine); Electron-Poor Biphenyl-Type Ligands for Transition Metal Catalysts. Tetrahedron: Asymmetry 1994, 5, 1297-1320.
97. 5-Phosphaphenanthren. Chem. Ber. 1982, 115, 1367-1373. For "BIPHEMP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethyl-1,1′-biphenyl), see: Svensson, G.; Albertsson, J.; Frejd, T.; Klingstedt, T. [(+)-(R)-2,2′-Bis(diphenylphosphino)-6,6′-dimethylbiphenyl](8,9,10- trinorborna-2,5-diene)rhodium(I) Tetrafluoroborate. Acta Crystallogr., Sect. C 1986, 42, 1324-1327. Schmid, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hansen, H.-J. Axially Dissymmetric Bis(triary)phosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine) ('BIPHEMP') and Analogues, and their Use in Rh-(I)-Catalyzed Asymmetric Isomerization of N,N-Diethylnerylamine. Helv. Chim. Acta 1988, 71, 897-929. For "BICHEPs" (2,2′-bis-(dicyclohexylphosphanyl)-6,6′-dimethyl-1,1′- biphenyl), see: Chiba, T.; Miyashita, A.; Nohira, H. Synthesis of Chiral Rh-BICHEP Complexes, Highly Efficient Catalysts for Asymmetric Hydrogenations. Tetrahedron Lett. 1991, 32, 4745-4748. For "MeO-BIPHEP" (2,2′-bis(diphenylphosphanyl)-6,6′-dimethoxy-1,1′-biphenyl), see: Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Axially Disymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)-('MeO- BIPHEP') and Analogues via an ortho-Lithiation/Iodination Ullmann-Reaction Approach. Helv. Chim. Acta 1991, 74, 370-389. Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter, U. New developments in enantioselective hydrogenation. Pure Appl. Chem. 1996, 68, 131-138. Trabesinger, G.; Albinati, A.; Feiken, N.; Kunz, R. W.; Pregosin, P. S.; Tschoerner, M. Enantioselective Homogeneous Catalysis and the "3,5-Dialkyl Meta-Effect". MeO-BIPHEP Complexes Related to Heck, Allylic Alkylation, and Hydrogenation Chemistry. J. Am. Chem. Soc. 1997, 119, 6315-6323. For 2,2′-bis(diphenylphosphanyl)-6,6′-difluoro-1,1′-biphenyl, see: Jendralla, H.; Li, C.-H.; Paulus, E. Efficient Synthesis of (R)- and (S)-(6,6′-Difluorobiphenyl-2,2′-diyl)bis(diphenylphosphine); Electron-Poor Biphenyl-Type Ligands for Transition Metal Catalysts. Tetrahedron: Asymmetry 1994, 5, 1297-1320.
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