Kinetic aspects of nonlinear effects in asymmetric catalysis

Accounts of Chemical Research

Volumn 33, Issue 6, 2000, Pages 402-411

  Blackmond, Donna G ^a  

^a UNIVERSITY OF HULL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE; ORGANOMETALLIC COMPOUND; ZINC;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMISTRY; CHIRALITY; CONFORMATION; DIMERIZATION; DISSOCIATION; ENANTIOMER; KINETICS; MODEL; NONLINEAR SYSTEM; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STOICHIOMETRY;

ALDEHYDES; CATALYSIS; DIMERIZATION; KETONES; KINETICS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; ZINC;

EID: 0033921344     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar990083s     Document Type: Article

References (40)

1. Horeau, A.; Guetté, J. P. Interactions Diastereomeres D'Antipodes en Phase Liquide. Tetrahedron 1974, 30, 1923-1931.
2. Horeau, A. Interactions D'Enantiomeres en Solution: Influence sur le Pouvoir Rotoire: Pureté Optique et Pureté Enantiomerique. Tetrahedron Lett. 1969, 36, 3121-3124.
3. Williams, T.; Pitcher, R. G.; Bommer, P.; Gutzwiller, J.; Uskovic, M. Diastereomeric Solute-Solute Interactions of Enantiomers in Achiral Solvents. Nonequivalence of the Nuclear Magnetic Resonance Spectra of Racemic and Optically Active Dihydroquinine. J. Am. Chem. Soc. 1969, 91, 1871-1872.
4. Wynberg, H.; Feringa, B. Enantiomeric Recognition and Interactions, Tetrahedron 1976, 32, 2831-2834.
5. (a) Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. Nonlinear Effects in Asymmetric Synthesis. Examples in Asymmetric Oxidations and Aldolization Reactions. J. Am. Chem. Soc. 1986, 108, 2353-2357.
6. (b) Guillaneux, D.; Zhao, S. H.; Samuel, O.; Rainford, D.; Kagan, H. B. Nonlinear Effects in Asymmetric Catalysis. J. Am. Chem. Soc. 1994, 116, 9430-9439.
7. Recent reviews: (a) Girard, C.; Kagan, H. B. Nonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation. Angew. Chem. 1998, 110, 3088-3127; Angew. Chem., Int. Ed. 1998, 37, 2922.
8. Recent reviews: (a) Girard, C.; Kagan, H. B. Nonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation. Angew. Chem. 1998, 110, 3088-3127; Angew. Chem., Int. Ed. 1998, 37, 2922.
9. (b) Kagan, H. B.; Girard, C.; Guillaneux, D.; Rainford, D.; Samuel, O.; Zhang, S. Y.; Zhao, S. H. Nonlinear Effects in Asymmetric Catalysis: Some Recent Aspects. Acta Chem. Scand. 1996, 30, 345-352.
10. (c) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Nonlinear Stereochemical Effects in Asymmetric Reactions, Tetrahedron Asymmetry 1997, 8, 2997-3017.
11. (d) Bolm, C. Nonlinear Effects in Enantioselective Synthesis: Asymmetric Amplification. In Advanced Asymmetric Synthesis; Stephenson, G. R., Ed.; Blackie A&P: Glasgow, 1996; pp 9-26.
12. (a) Blackmond, D. G. Mathematical Models of Nonlinear Effects in Asymmetric Catalysis: New Insights Based on the Role of Reaction Rate. J. Am. Chem. Soc. 1997, 119, 12934-12939.
13. (b) Blackmond, D. G. Kinetic Implications of Nonlinear Effects in Asymmetric Synthesis. J. Am. Chem. Soc. 1998, 120, 13349-13353.
14. (c) Blackmond, D. G. Nonlinear Effects in Asymmetric Catalysis: Implications for Synthetic Strategies. In Catalysis of Organic Reactions; Herkes, F., Ed.; Marcel Dekker: New York, 1998; pp 455-465.
15. (d) Blackmond, D. G.; Rosner, T.; Neugebauer, T.; Reetz, M. T. Kinetic Influences on Enantioselectivity for Non-Diastereopure Catalyst Mixtures. Angew. Chem. 1999, 111, 2333-2335; Angew. Chem., Int. Ed. 1999, 38, 2196-2199.
16. (d) Blackmond, D. G.; Rosner, T.; Neugebauer, T.; Reetz, M. T. Kinetic Influences on Enantioselectivity for Non-Diastereopure Catalyst Mixtures. Angew. Chem. 1999, 111, 2333-2335; Angew. Chem., Int. Ed. 1999, 38, 2196-2199.
17. (a) Noyori, R.; Kitamura, M. Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds-Chirality Transfer, Multiplication, and Amplification. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
18. (b) Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800.
19. 2 model.
20. Practical exploitation of asymmetric amplification may involve cases where the removal of a small impurity of the opposite ligand is difficult or uneconomical. See, for example, the section on stoichiometric asymmetric synthesis and the work of ref 23.
21. +-catalyzed hydrogenation of enamides that reaction rates are much faster when the achiral DIPHOS ligand is used compared to enantiopure asymmetric ligands such as CHIRAPHOS or DIPAMP, and he has suggested that selectivity at the price of activity is an inevitable feature of these asymmetric catalytic reactions. Halpern, J. Asymmetric Catalytic Hydrogenation: Mechanism and Origin of Enantioselection. In Asymmetric Synthesis, Vol. 5: Chiral Catalysis; Morrison, J. D., Ed.; Academic Press, New York, 1985; Chapter 2, pp 41-69.
22. The development of the models in this section is published here for the first time.
23. (a) Girard, C.; Kagan, H. B. Nonlinear Effect in the Reduction of Acetophenone by Diisopinocampheyl Chloroborane: Influence of the Reagent Preparation. Tetrahedron: Asymmetry 1995, 6, 1881-1884.
24. (b) Mikami, K.; Motoyama, Y.; Terada, M. Asymmetric Catalysis of Diels-Alder Cycloadditions by an MS-Free Binaphthol-Titanium Complex-Dramatic Effect of MS, Linear vs Positive Nonlinear Relationship, and Synthetic Applications. J. Am. Chem Soc. 1994, 116, 2812-2820.
25. Oguni, N.; Matsuda, Y.; Kaneko, T. Asymmetric Amplifying Phenomena in Enantioselective Addition of Diethylzinc to Benzaldehyde. J. Am. Chem Soc. 1988, 110, 7877-7888.
26. A model similar to that described in ref 8b was recently published: (a) Gutman, I. A Simple Model for Chiral Amplification in the Aminoalcohol-Catalyzed Reaction of Aldehydes with Dialkylzinc. J. Serb. Chem. Soc. 1999, 64, 447-452.
27. (b) Gutman, I. A Note on the Noyori Model for Chiral Amplification in the Aminoalcohol-Catalyzed Reaction of Aldehydes with Dialkylzinc. J. Serb. Chem. Soc. 1999, 64, 681-684.
28. (a) Mikami, K.; Terada, M. Chiral Titanium Complex-Catalyzed Carbonyl-Ene Reaction with Glyoxylate: Remarkable Positive Nonlinear Effect. Tetrahedron 1992, 48, 5671-5680.
29. 3-oxo Titanium Catalyst. Inorg. Chim. Acta 1999, 296, 267-272. In this recent paper the authors also suggest that the trimer itself may be the active catalyst.
30. A 6-fold and a 3-fold suppression reaction rate using a racemic mixture compared to the enantiopure catalyst are predicted for the irreversible and reversible models, respectively.
31. de Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L Enantioselective Conjuate Addition of Diethylzinc to Chalcones Catalysed by Chiral Ni(II) Aminoalcohol Complexes. Tetrahedron 1994, 50, 4479-4491.
32. Bolm, C.; Ewald, M.; Felder, M. Catalytic Enantioselective Conjugate Addition of Dialkylzinc Compounds to Chalcones. Chem. Ber. 1992, 125, 1205-1215.
33. prod at a given instant in the reaction, in the absence of the reaction's prior history, and may be calculated from successive cumulative values.
34. prod in experiments where substrate was added during reaction. However, the substrate conversion level used for comparison was lower (ca. 40%) than that at which Figures 8 and 9 suggest that substrate effects become significant.
35. Chandrasekharan, J.; Ramachandran, P. V.; Brown, H. C. Diisopinocampheylchloroborane, a Remarkably Efficient Chiral Reducing Agent for Aromatic Prochiral Ketones. J. Org. Chem. 1985, 50, 5446-5448.
36. Zhao, M.; King, A. O.; Larsen, R. D.; Verhoeven, T. R.; Reider, R. J. A Convenient and Economical Method for the Preparation of DIP-Chloride™ and Its Application in the Asymmetric Reduction of Aralkyl Ketones. Tetrahedron Lett. 1997, 38, 2641-2644.
37. Nonlinear effects in systems where the reaction products are enantiomeric but the catalysts are diastereomers or pseudodiastereomers were first studied by Kagan and co-workers: Zhang, S. Y.; Girard, C.; Kagan, H. B. Nonlinear Effects Involving Two Competing Pseudo-Enantiomeric Catalysts: Example in Asymmetric Dihydroxylation of Olefins. Tetrahedron: Asymmetry 1995, 6, 2637-2640.
38. Reetz, M. T.; Neugebauer, T. New Diphosphite Ligands for Catalytic Asymmetric Hydrogenation: The Crucial Role of Conformationally Enantiomeric Diols. Angew. Chem. 1999, 111, 134; Angew. Chem., Int. Ed. 1999, 38, 179.
39. Reetz, M. T.; Neugebauer, T. New Diphosphite Ligands for Catalytic Asymmetric Hydrogenation: The Crucial Role of Conformationally Enantiomeric Diols. Angew. Chem. 1999, 111, 134; Angew. Chem., Int. Ed. 1999, 38, 179.
40. Bolm, C.; Muniz, K.; Hildebrand, J. P. Planar-Chiral Ferrocenes in Asymmetric Catalysis: The Impact of Stereochemically Inhomogeneous Ligands. Org. Lett. 1999, 1, 491-494.