Origin of enantioselectivity in asymmetric hydrovinylations catalyzed by phosphoramidite nickel catalysts: An experimentally supported density functional study

Organometallics

Volumn 23, Issue 23, 2004, Pages 5606-5617

  Hölscher, Markus ^a   Franciò, Giancarlo ^a   Leitner, Walter ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CATALYSTS; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; PROBABILITY DENSITY FUNCTION; RATE CONSTANTS;

ENANTIOSELECTIVELY; LIGANDS; REACTION PATHS; SOLVENT EFFECTS;

NICKEL;

EID: 9144243036     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om040107l     Document Type: Article

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15. Catalytic reactions employing 7 as the ligand: Copper-catalyzed asymmetric diethylzinc addition to enones: Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. Iridium-catalyzed substitution of allylic acetates: Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741. Copper-catalyzed allylic alkylations: Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169. Rhodium-catalyzed asymmetric olefin hydrogenations: van den Berg, M.; Haak, R. M.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Adv. Synth. Catal. 2002, 344, 1003. Pena, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552. van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Jaljaars, C. E. P.; Williams, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 208. Palladium-catalyzed asymmetric Heck reactions: Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184. Rhodium-catalyzed asymmetric arylation of enones: Imbos, R. Dissertation, University of Groningen, 2002. Palladium-catalyzed asymmetric hydrogenations of olefins: Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558. Iridium catalyzed allylic amination and etherification: Ohmura, T.; Hartwig, J. F.; J. Am. Chem. Soc. 2002, 124, 15164. Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
16. Catalytic reactions employing 7 as the ligand: Copper-catalyzed asymmetric diethylzinc addition to enones: Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. Iridium-catalyzed substitution of allylic acetates: Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741. Copper-catalyzed allylic alkylations: Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169. Rhodium-catalyzed asymmetric olefin hydrogenations: van den Berg, M.; Haak, R. M.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Adv. Synth. Catal. 2002, 344, 1003. Pena, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552. van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Jaljaars, C. E. P.; Williams, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 208. Palladium-catalyzed asymmetric Heck reactions: Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184. Rhodium-catalyzed asymmetric arylation of enones: Imbos, R. Dissertation, University of Groningen, 2002. Palladium-catalyzed asymmetric hydrogenations of olefins: Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558. Iridium catalyzed allylic amination and etherification: Ohmura, T.; Hartwig, J. F.; J. Am. Chem. Soc. 2002, 124, 15164. Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
17. Catalytic reactions employing 7 as the ligand: Copper-catalyzed asymmetric diethylzinc addition to enones: Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. Iridium-catalyzed substitution of allylic acetates: Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741. Copper-catalyzed allylic alkylations: Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169. Rhodium-catalyzed asymmetric olefin hydrogenations: van den Berg, M.; Haak, R. M.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Adv. Synth. Catal. 2002, 344, 1003. Pena, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552. van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Jaljaars, C. E. P.; Williams, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 208. Palladium-catalyzed asymmetric Heck reactions: Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184. Rhodium-catalyzed asymmetric arylation of enones: Imbos, R. Dissertation, University of Groningen, 2002. Palladium-catalyzed asymmetric hydrogenations of olefins: Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558. Iridium catalyzed allylic amination and etherification: Ohmura, T.; Hartwig, J. F.; J. Am. Chem. Soc. 2002, 124, 15164. Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
18. Catalytic reactions employing 7 as the ligand: Copper-catalyzed asymmetric diethylzinc addition to enones: Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. Iridium-catalyzed substitution of allylic acetates: Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741. Copper-catalyzed allylic alkylations: Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169. Rhodium-catalyzed asymmetric olefin hydrogenations: van den Berg, M.; Haak, R. M.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Adv. Synth. Catal. 2002, 344, 1003. Pena, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552. van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Jaljaars, C. E. P.; Williams, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 208. Palladium-catalyzed asymmetric Heck reactions: Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184. Rhodium-catalyzed asymmetric arylation of enones: Imbos, R. Dissertation, University of Groningen, 2002. Palladium-catalyzed asymmetric hydrogenations of olefins: Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558. Iridium catalyzed allylic amination and etherification: Ohmura, T.; Hartwig, J. F.; J. Am. Chem. Soc. 2002, 124, 15164. Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
19. Catalytic reactions employing 7 as the ligand: Copper-catalyzed asymmetric diethylzinc addition to enones: Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. Iridium-catalyzed substitution of allylic acetates: Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741. Copper-catalyzed allylic alkylations: Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169. Rhodium-catalyzed asymmetric olefin hydrogenations: van den Berg, M.; Haak, R. M.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Adv. Synth. Catal. 2002, 344, 1003. Pena, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552. van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Jaljaars, C. E. P.; Williams, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 208. Palladium-catalyzed asymmetric Heck reactions: Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184. Rhodium-catalyzed asymmetric arylation of enones: Imbos, R. Dissertation, University of Groningen, 2002. Palladium-catalyzed asymmetric hydrogenations of olefins: Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558. Iridium catalyzed allylic amination and etherification: Ohmura, T.; Hartwig, J. F.; J. Am. Chem. Soc. 2002, 124, 15164. Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
20. Catalytic reactions employing 7 as the ligand: Copper-catalyzed asymmetric diethylzinc addition to enones: Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. Iridium-catalyzed substitution of allylic acetates: Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741. Copper-catalyzed allylic alkylations: Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169. Rhodium-catalyzed asymmetric olefin hydrogenations: van den Berg, M.; Haak, R. M.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Adv. Synth. Catal. 2002, 344, 1003. Pena, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552. van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Jaljaars, C. E. P.; Williams, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 208. Palladium-catalyzed asymmetric Heck reactions: Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184. Rhodium-catalyzed asymmetric arylation of enones: Imbos, R. Dissertation, University of Groningen, 2002. Palladium-catalyzed asymmetric hydrogenations of olefins: Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558. Iridium catalyzed allylic amination and etherification: Ohmura, T.; Hartwig, J. F.; J. Am. Chem. Soc. 2002, 124, 15164. Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
21. Catalytic reactions employing 7 as the ligand: Copper-catalyzed asymmetric diethylzinc addition to enones: Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. Iridium-catalyzed substitution of allylic acetates: Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741. Copper-catalyzed allylic alkylations: Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169. Rhodium-catalyzed asymmetric olefin hydrogenations: van den Berg, M.; Haak, R. M.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Adv. Synth. Catal. 2002, 344, 1003. Pena, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552. van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Jaljaars, C. E. P.; Williams, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 208. Palladium-catalyzed asymmetric Heck reactions: Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184. Rhodium-catalyzed asymmetric arylation of enones: Imbos, R. Dissertation, University of Groningen, 2002. Palladium-catalyzed asymmetric hydrogenations of olefins: Jensen, J. F.; Svendsen, B. Y.; La Cour, T. V.; Pedersen, H. L.; Johannsen, M. J. Am. Chem. Soc. 2002, 124, 4558. Iridium catalyzed allylic amination and etherification: Ohmura, T.; Hartwig, J. F.; J. Am. Chem. Soc. 2002, 124, 15164. Lopez, F.; Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 3426.
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