Chiral monodentate phosphine ligand MOP for transition-metal-catalyzed asymmetric reactions

Accounts of Chemical Research

Volumn 33, Issue 6, 2000, Pages 354-362

  Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ESTER DERIVATIVE; FORMIC ACID; HEAVY METAL; LIGAND; METAL; NAPHTHALENE DERIVATIVE; NAPHTHYL GROUP; ORGANOMETALLIC COMPOUND; PALLADIUM; PHOSPHINE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHELATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; CHIRALITY; CONFORMATION; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

CATALYSIS; LIGANDS; METALS, HEAVY; MOLECULAR CONFORMATION; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHOSPHINES; SILANES;

EID: 0033947876     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar990080f     Document Type: Article

References (41)

1. For a recent pertinent review see: Jacobsen, E. N.; Pfaltz, A.; Yamamoto H. Comprehensive Asymmetric Catalysis; Springer: New York, 1999; Vols. 1-3.
2. Knowles, W. S.; Sabacky, M. J. Catalytic Asymmetric Hydrogenation Employing a Soluble, Optically Active, Rhodium Complex. Chem. Commun. 1968, 1445.
3. Horner, L.; Siegel, H.; Büthe, H. Asymmetrische Katalytische Hydrierung mit einen Homogen Gelösten Optish Aktiven Phosphin-Rhodium-Komplex. Angew. Chem. 1968, 80, 1034.
4. Kagan, H. B.; Dang, T. P. Asymmetric Catalytic Reduction with Transition Metal Complexes. I. A Catalytic System of Rhodium(I) with (-)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane, a New Chiral Diphosphine. J. Am. Chem. Soc. 1972, 94, 6429.
5. Noyori, R.; Takaya, H. BINAP: An Efficient Chiral Element for Asymmetric Catalysis. Acc. Chem. Res. 1990, 23, 345.
6. Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, 1995; pp 105-142.
7. Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. Catalytic Asymmetric Hydrogenation. J. Chem. Soc., Chem. Commun. 1972, 10.
8. Morrison, J. D.; Burnett, R. E.; Aguiar, A. M.; Morrow, C. J.; Phillips, C. Asymmetric Homogeneous Hydrogenation with Rhodium(I) Complexes of Chiral Phosphines. J. Am. Chem. Soc. 1971, 93, 1301.
9. Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. Practical Asymmetric Synthesis of 1,1′-Binaphthyls via Asymmetric Cross-Coupling with a Chiral (Alkoxyalkylferrocenyl)monophosphine-Nickel Catalyst. J. Am. Chem. Soc. 1988, 110, 8153.
10. Kurz, L.; Lee, G., Morgans, D., Jr.; Waldyke, M. J.; Ward, T. Stereospecific Functionalization of (R)-(-)-1,1′-Bi-2-naphthol Triflate. Tetrahedron Lett. 1990, 31, 6321.
11. Uozumi, Y.; Hayashi, T. Catalytic Asymmetric Synthesis of Optically Active 2-Alkanols via Hydrosilylation of 1-Alkenes with a Chiral Monophosphine-Palladium Catalyst. J. Am. Chem. Soc. 1991, 113, 9887.
12. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. Synthesis of Optically Active 2-(Diarylphosphino)-1,1′-binaphthyls, Efficient Chiral Monodentate Phosphine Ligands. J. Org. Chem. 1993, 58, 1945.
13. Hattori, T.; Sijo, M.; Kumagai, S.; Miyano, S. Enantiomeric 2′-Methoxy-1,1′-binaphthyl-2-carboxylic Acid as the Starting Material for the Stereospecific Synthesis of Optically Pure 2′-Methoxy-1,1′-binaphthyls. Chem. Express 1991, 6, 335.
14. Uozumi, Y.; Suzuki, N.; Ogiwara, A.; Hayashi, T. Preparation of Optically Active Binaphthylmonophosphines (MOP's) Containing Various Functional Groups. Tetrahedron 1994, 50, 4293.
15. Hayashi, T.; Iwamura, H.; Uozumi, Y.; Matsumoto, Y.; Ozawa, F. A New Optically Active Monodentate Phosphine Ligand, (R)-(+)-3-Diphenylphosphino-3′-methoxy-4,4′-biphenanthryl (MOP-phen). Preparation and Use for Palladium-Catalyzed Asymmetric Reduction of Allylic Esters with Formic Acid. Synthesis 1994, 526.
16. Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. Catalytic Asymmetric Synthesis of Axially Chiral Biaryls by Palladium-Catalyzed Enantioposition-Selective Cross-Coupling. J. Am. Chem. Soc. 1995, 117, 9101.
17. Uozumi, Y.; Kitayama, K.; Hayashi, T.; Yanagi, K.; Fukuyo, E. Asymmetric Hydrosilylation of 1-Alkenes Catalyzed by Palladium-MOP. Bull. Chem. Soc. Jpn. 1995, 68, 713.
18. Hayashi, T.; Iwamura, H.; Naito, M.; Matsumoto, Y.; Uozumi, Y.; Miki, M.; Yanagi, K. Catalytic Asymmetric Reduction of Allylic Esters with Formic Acid Catalyzed by Palladium-MOP Complexes. J. Am. Chem. Soc. 1994, 116, 775.
19. Tamao, K. In Advances in Silicon Chemistry; Larson, G. L., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, pp 1-62.
20. Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1989; p 1479.
21. Uozumi, Y.; Lee, S.-Y.; Hayashi, T. Asymmetric Functionalization of Bicycloalkenes by Catalytic Enantioposition-Selective Hydrosilylation. Tetrahedron Lett. 1992, 33, 7185.
22. Uozumi, Y.; Hayashi, T. Asymmetric Hydrosilylation of Dihydrofurans by Use of Palladium-MOP Catalyst. Tetrahedron Lett. 1993, 34, 2335.
23. Kitayama, K.; Uozumi, Y.; Hayashi, T. Palladium-Catalysed Asymmetric Hydrosilylation of Styrenes with a New Chiral Monodentate Phosphine Ligand. J. Chem. Soc., Chem. Commun. 1995, 1533.
24. Kitayama, K.; Tsuji, H.; Uozumi, Y.; Hayashi, T. Asymmetric Hydrosilylation of Cyclic 1,3-Dienes Catalyzed by an Axially Chiral Monophosphine-Palladium Complex. Tetrahedron Lett. 1996, 37, 4169.
25. Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1995.
26. Hayashi, T.; Iwamura, H.; Uozumi, Y. Asymmetric Synthesis of Allylsilanes by Palladium-Catalyzed Asymmetric Reduction of Allylic Carbonates with Formic Acid. Tetrahedron Lett. 1994, 35, 4813.
27. Hayashi, T.; Kawatsura, M.; Iwamura, H.; Yamaura, Y.; Uozumi, Y. Catalytic Asymmetric Synthesis of Optically Active Alkenes by Palladium-Catalysed Asymmetric Reduction of Racemic Allylic Esters with Formic Acid. J. Chem. Soc., Chem. Commun. 1996, 1767.
28. Kawatsura, M.; Uozumi, Y.; Ogasawara, M.; Hayashi, T. Palladium-Catalyzed Asymmetric Reduction of Racemic Allylic Esters with Formic Acid: Effects of Phosphine Ligands on Isomerization of π-Allylpalladium Intermediates and Enantioselectivity. Tetrahedron 2000, 56, 2247.
29. Hayashi, T.; Kawatsura, M.; Uozumi, Y. Regio- and Enantioselective Allylic Alkylation Catalyzed by Chiral Monophosphine-Palladium Complexes. Chem. Commun. 1997, 561.
30. Hayashi, T.; Kawatsura, M.; Uozumi, Y. Retention of Regiochemistry of Allylic Esters in Palladium-Catalyzed Allylic Alkylation in the Presence of a MOP Ligand. J. Am. Chem. Soc. 1998, 120, 1681.
31. Matsumoto, Y.; Naito, M.; Hayashi, T. Palladium(0)-Catalyzed Hydroboration of 1-Buten-3-ynes: Preparation of Allenylboranes. Organometallics 1992, 11, 2732.
32. Matsumoto, Y.; Naito, M.; Uozumi, Y.; Hayashi, T. Axially Chiral Allenylboranes: Catalytic Asymmetric Synthesis by Palladium-Catalysed Hydroboration of 1-Buten-3-ynes and Their Reaction with an Aldehyde. J. Chem. Soc., Chem. Commun. 1993, 1468.
33. Tsuji, Y.; Kusui, T.; Kojima, T.; Sugiura, Y.; Yamada, N.; Tanaka, S.; Ebihara, M.; Kawamura, T. Palladium-Complex-Catalyzed Cyanation of Allylic Carbonates and Acetates Using Trimethylsilyl Cyanide. Organometallics 1998, 17, 4835.
34. Imada, Y.; Fujii, M.; Kubota, Y.; Murahashi, S.-I. Palladium-Catalyzed Asymmetric Alkoxycarbonylation of Allyl Phosphates. Tetrahedron Lett. 1997, 38, 8227.
35. Oppolzer, W.; Kuo, D. L.; Hutzinger, M. W.; Léger, R.; Durand, J.-O.; Leslie, C. Studies Towards Asymmetric Catalyzed Metallo-ene Reactions. Tetrahedron Lett. 1997, 38, 6213.
36. Hanzawa, Y.; Tabuchi, N.; Saito, K.; Noguchi, S.; Taguchi, T. Acylzirconocene Chloride as an "Unmasked" Acyl Anion: Enantioselective 1,2-Addition to α, β-Unsaturated Ketone Derivatives. Angew. Chem., Int. Ed. 1999, 38, 2395.
37. RajanBabu, T. V.; Nomura, N.; Jin, J.; Radetich, B.; Park, H.; Nandi, M. Hydrovinylation and Related Reactions: New Protocols and Control Elements in Search of Greater Synthetic Efficiency and Selectivity. Chem. Eur. J. 1999, 5, 1963.
38. Sato, Y.; Nishiyama, T.; Mori, M. Asymmetric Synthesis of Isoindoline and Isoquinoline Derivatives Using Nickel(0)-Catalyzed [2+2+2] Cocyclization. J. Org. Chem. 1994, 59, 6133.
39. Stará, I. G.; Stary, I.; Kollárovic, A.; Teply, F.; Vyskocil, S.; Saman, D. Transition Metal Catalysed Synthesis of Tetrahydro Derivatives of [5]-, [6]-, and [7]Helicene. Tetrahedron Lett. 1999, 40, 1993.
40. Sakai, M.; Ueda, M.; Miyaura, N. Rhodium-Catalyzed Addition of Organoboronic Acids to Aldehydes. Angew. Chem., Int. Ed. 1998, 37, 3279.
41. Hayashi, T.; Ishigedani, M. Rhodium-Catalyzed Asymmetric Arylation of Imines with Organostannanes. Asymmetric Synthesis of Diarylmethylamines. J. Am. Chem. Soc. 2000, 122, 976.