Organic compounds -- part of the class 532-570 series – Organic compounds – Heavy metal containing
Patent
1992-11-10
1995-08-08
O'Sullivan, Peter
Organic compounds -- part of the class 532-570 series
Organic compounds
Heavy metal containing
556 28, C07F 108
Patent
active
054400627
ABSTRACT:
The conjugate addition of hydrocarbon equivalents to alpha,beta-unsaturated carbonyl compounds using a series of novel catalysts is described. The catalysts comprise copper(I) complexes with ligand systems comprising either tropocoronand macrocycles or N,N'-dialkylsubstituted aminotroponeimines.
REFERENCES:
patent: 3052705 (1962-09-01), Brasen et al.
patent: 3177232 (1965-04-01), Muetterties
patent: 3876675 (1975-04-01), Trofimenko
patent: 4471130 (1984-09-01), Katsuki et al.
Grant J., Hackh's Chemical Dictionary, Fourth Ed. McGraw-Hill Book Company. (1969) New York, p. 331.
Brunner, H. and Knott, A., "Asymmetric Catalyses XXVII*. Rh Complexes with Optically Active Ligands Derived from Tropolone," J. of Organometallic Chemistry, 295:211-221 (1985).
Posner, G. H. and Hulce, M., "Enantiocontrolled Synthesis of (S)-3-Substituted Cycloalkanones from (S)-2-(p-Tolylsulfinyl)-2-Cycloalkenones and Diorganomagnesium Reagents," Tetrahedron Letters, 25(4):379-382 (1984).
Villacorta, G. M. and Lippard, S. J., "Tropocoronands: A Versatile Macrocyclic Ligand System for Mononuclear and Binuclear Metal Complexes," Pure & Appl. Chem., 58(11):1477-1484 (1986).
Villacorta, G. M., et al., "Dicopper(I) Tropocoronands: Synthesis, X-ray Crystal Structure, and Spectral properties of Neutral Binuclear Copper(I) Complexes Bridged by Symmetrically Substituted Alkynes," J. Am. Chem. Soc., 107:6732-6734 (1985).
Dieter, R. K. and Tokles, M., "Asymmetric Induction in the Conjugate Addition Reactions of Chiral Organo(hetero)cuprates," J. Am. Chem. Soc., 109:2040-2046 (1987).
Lipshutz, B. H., et al., "The Chemistry of Higher Order Organocuprates," Tetrahedron, 40(24):5005-5038 (1984).
Lipshutz, B. H., et al., "Substitution Reactions of Secondary Halides and Epoxides with Higher Order, Mixed Organocuprates, R.sub.2 Cu(CN)Li.sub.2 : Synthetic, Stereochemical, and Mechanistic Aspects," J. Org. Chem., 49:3928-3938 (1984).
Corey, E. J., et al., "Enantioselective Conjugate Addition of Rationally Designed Chiral Cuprate Reagents to 2-Cycloalkenones," J. Am. Chem. Soc., 108:7114-7116 (1986).
Davis, W. M. and Lippard, S. J., "Tropocoronands as Binucleating Ligands. Synthesis, Structure and Properties of a (.mu.-Acetato)(.mu.-methoxo)dicopper(II) Derivative," Inorg. Chem., 24:3688-3691 (1985).
Villacorta, G. M., et al., "Alkyne-Bridged Dicopper(I) Complexes of the Tropocoronand Macrocycles," Organometallics, 6:2426-2431 (1987).
Villacorta, G. M. and Lippard, S. J., "Dicopper(I) Carbonyl Tropocoronands. Preparation, Structural Characteristics and Reactivity of Neutral Binuclear Cu-CO Macrocyclic Compounds," Inorg. Chem., 26:3672-3676 (1987).
Villacorta, G. M. and Lippard, S. J., "Synthesis, Structure Determination and Stereoisomerism of Dirhodium(I) Tetracarbonyl Tropocoronand Complexes," Inorg. Chem., 27:144-149 (1988).
Villacorta, G. M., et al., "Synthesis and Reactivity of Binuclear Tropocoronand and Related Organocopper(I) Complexes, Catalytic Enantioselective Conjugate Addition of Grignard Reagents to 2-Cyclohexen-1-one," J. Am. Chem. Soc., 110:3175-3182 (1988).
Fryzuk, M. D. and Bosnich, B., "Asymmetric Synthesis. An Asymmetric Homogeneous Hydrogenation Catalyst Which Breeds Its Own Chirality," J. Am. Chem. Soc., 100:5491-5494 (1978).
Eaton, D. R., et al., "Synthesis and Magnetic Resonance Studies of Some Paramagnetic Transition Metal Aminotroponiminates," Inorg. Chem., 7(10):2040-2046 (1968). (From Chem. Abstracts, 1968, 69, Abstract No. 22).
Bertz, S. H., et al., "Asymmetric Induction with Amidocuprates," J. Org. Chem., 51:4953-4959 (1986).
Ahn Kwang-Hyun
Lippard Stephen J.
Villacorta Gilberto M.
Massachusetts Institute of Technology
O'Sullivan Peter
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