Organic compounds -- part of the class 532-570 series – Organic compounds – Heavy metal containing
Patent
1995-06-06
1997-09-02
Nazario-Gonzalez, Porfirio
Organic compounds -- part of the class 532-570 series
Organic compounds
Heavy metal containing
502167, 549337, 549510, 549524, 549525, 549531, 549533, 556 32, 556 34, 556 42, 556 56, 556 57, 556150, 556137, 568 27, C07F 1300, C07F 900, C07F 700, C07F 1500
Patent
active
056633939
ABSTRACT:
Chiral catalysts for enantioselectively epoxidizing a prochiral olefin and for enantioselectively oxidizing a prochiral sulfide are disclosed, together with methods of using such catalysts. In accordance with one aspect of the invention, the catalyst is a salen derivative which has the following general structure: ##STR1## In accordance with another aspect of the present invention is a method of, producing an epoxychroman using a chiral catalyst. In accordance with this method, a chromene derivative, an oxygen atom source, and a chiral catalyst are reacted under such conditions and for such time as is needed to epoxidize said chromene derivative. In accordance with yet another aspect of this invention is a method of enantioselectively epoxidizing a cis-cinnamate derivative to make taxol or an analog thereof. In accordance with another aspect a method of disproportionation of hydrogen peroxide using the catalysts of the present invention is disclosed.
REFERENCES:
patent: 4924011 (1990-05-01), Denis et al.
Akbulut, et al., "The Triplex Diels-Alder Reaction of 1,3-Dienes with Enol, Alkene, and Acetylenic Dienophiles: Scope and Utility," J. Org. Chem., vol. 54, No. 11, 1989, pp. 2549-2556.
Banfi, et al., "Investigation on Factors Ruling Catalytic Efficiency and Chemical Stability of Mn(III) Porphyrins in HOCI Olefin Epoxidation; Conditions for Practical Application," J. Org. Chem., vol. 54, No. 8, 1989.
Bergmann, et al., "4-Heterocyclyloxy-2H-1-benzopyran Potassium Channel Activators," J. of Medicinal Chem., 1990, vol. 33, No. 10, pp. 2759-2767.
Borman, Chem. & Eng. News, Sep. 2, 1991, pp. 11-18.
Boucher, J. Inorg. Nucl. Chem., vol. 36, p. 531 (1974).
Casiraghi, et al., "Selective Reactions Between Phenols and Formaldehyde. A Novel Route to Salicylaldehydes", J.C.S. Perkin I, 1980, pp. 1862-1865.
Cesarotti, et al., "Optically Active Complexes of Schiff Bases. Part 6..sup.1 Palladium(II) and Platinum(II) Complexes with Quadridentate Schiff Bases of Salicylaldehyde", J.C.S. Dalton, 1981, pp. 2147-2152.
Che, et al., "Manganese(III) Amide Complexes as a New Class of Catalyst for Efficient Alkene Epoxidation", J. Chem. Soc., Chem. Commun., 1986, pp. 1443-1444.
Coleman et al., "Characterization and Electrochemistry of Manganese(III) Complexes Containing Pentadentate Ligands," Inorg. Chem. vol. 20, No. 4, 1253-1258 (1981).
Collins, et al. "A Water-Stable Manganese(V)-Oxo Complex: Definitive Assignment of a Infrared Vibration," J. Am. Chem. Soc., vol. 112, No. 2, 899-901, (1990).
Collins, et al., "A Manganese (V)-Oxo Complex," J. Am. Chem. Soc., vol. 111, No. 12, 4511-4513, (1989).
Colombo, et al., "Chiral Induction in the Oxidation of Thioanisole with Chiral Oxotitanium(IV) Schiff Bases Complexes as Catalysts. The Importance of the Conformation of the Ligands", Gazz. Chim. Ital., pp. 35-40, (1986).
Corey, et al. "Practical Enantioselective Diels-Alder and Aldol Reactions Using a New Chiral Controller System," J. Am. Chem. Soc., vol. 111, No. 14, pp. 5493-5495, (1989).
Curci, et al., "Asymmetric Epoxidation of Unfunctionalized Alkenes by Dioxirane Intermediates Generated from Potassium Peroxomonosulphate and Chiral Ketones", J. Chem. Soc., Chem. Commun., pp. 155-156, (1984).
Davis, "Chemistry of Oxaziridines. 4..sup.1 Asymmetric Epoxidation of Unfunctionalized Alkenes Using Chiral 2-Sulfonyloxaziridines: Evidence for a Planar Transition State Geometry", J. Am. Chem. Soc., vol. 105, pp. 3123-3128, (1983).
Davis, et al., "Asymmetric Epoxidation of Nonfunctionalized Alkenes with High Enantioselectivity Using Chiral Sulfamyloxaziridines", Tetrahedron Letters, vol. 27 No. 42, pp. 5079-5082, (1986).
Denis et al., "A Highly Efficient, Practical Approach to Natural Taxol", J. Am. Chem. Soc., vol. 110, No. 17, pp. 5917-5919, (1988).
Fourneron, et al., "Microbial Transformations. 12. Regiospecific and Asymmetric Oxidation of the Remote Double Bond of Geraniol," J. Org. Chem., vol. 54, No. 19, pp. 4686-4689, (1989).
Ganeshpure et al., "Epoxidation of Alkenes with Iodosylbenzene Catalysed by a Water-Soluble Chromium (III) N,N-Ethylene bis(salicylideneaminato)(salen) Complex Using B-Cyclodextrin as a Phase Transfer Agent," J. Chem. Soc. Chem. Commun., 1988, pp. 981-982.
Gao, et al., "Catalytic Asymmetric Epoxidation and Kinetic Resolution: Modified Procedures Including in Situ Derivatization", J. Am. Chem. Soc., vol. 109, No. 19, pp. 5765-5780, (1987).
Goto et al., "Analysis of the Induction Period and Proposal of Mechanism of the Catalyst of 3-Methylindole Oxygenation by Two Isomers of N,N'-(1,2-Cyclohexylene) bis (3-tert-butylsalicylideneaminato) cobalt (II)", Chem. Pharm. Bull., 33(6), pp. 2195-2203 (1985).
Groves, et al., "Catalytic Asymmetric Epoxidations with Chiral Iron Porphyrins", J. Am. Chem. Soc., vol. 105, No. 18, pp. 5791-5796, (1983).
Groves, et al., "Asymmetric Hydroxylation, Epoxidation, and Sulfoxidation Catalyzed by Vaulted Binaphthyl Metalloporphyrins," J. Org. Chem., vol. 55, No. 11, 3628-3634, (1990).
Halterman et al., "Catalytic Asymmetric Epoxidation of Unfunctionalized Alkenes Using the First D.sub.4 -Symmetric Metallotetraphenylporphyrin", J. Org. Chem., 56:5253 (1991).
Hassine, et al., "Utilisation de la Synthese Atrolactique Pour L'Evaluation de L'Evaluation de L'Efficacite D'Inducteurs de Synthese Asymetrique", Bull. Soc. Chim. Belg., vol. 95, pp. 547-566, (1986).
Helder, et al., "Catalytic Asymmetric Induction in Oxidation Reactions", Tetra. Lett., No. 21, pp. 1831-1834, (1976).
Hopkins, et al., "Iron(III) Complexes of Chiral Bipyridine Macrocycles as Novel Metallocatalysts", J. Chem. Soc., Chem. Commun., 1987, pp. 171-173.
Hosoya, et al., "Enantioselective Epoxidation of Olefins with Chiral (Salen) Manganese (III) Complexes Bearing 4-Methyl-3-[R)-1phenylpropyl]salicylideneamine as a Constituent", Synlett, Sep. 1991, pp. 691-692.
Irie, et al., "Enantioselective Epoxidation of Unfunctionalized Olefins Using Chiral (Salen) Manganese (III) Complexes," Tetra. Lett., vol. 32, No. 8, pp. 1055-1058, 1991.
Irie, et al., "Catalytic Epoxidation with Molecular Oxygen Using Nickel Complex," Tetra. Lett., vol. 32, No. 47, pp. 6891-6894, 1991.
Irie et al., "Donor Ligand Effect in Asymmetric Epoxidation of Unfunctionalized Olefins with Chiral Salen Complexes," Synlett, Apr. 1991, pp. 265-266.
Irie, et al., "Catalytic Asymmetric Epoxidation of Unfunctionalized Olefins", Using Chiral (Salen) manganese (III) Complexes, Tetra., vol. 2, No. 7, pp. 481-494, 1991.
Irie, et al., "Catalytic Asymmetric Epoxidation of Unfunctionalized Olefins," Tetra. Lett., vol. 31, No. 50, pp. 7345-7348, 1990.
Jacobsen et al., "Electronic Tuning of Asymmetric Catalysts," J. Am. Chem. Soc., vol. 113, No. 17, 1991.
Jacobsen, et al., "Asymmetric Dihydroxylation via Ligand-Accelerated Catalysis," J. Am. Chem. Soc., vol. 110, No. 6, pp. 1968-1970, (1988).
Jacobsen et al., "Highly Enantioselective Epoxidation Catalysts Derived from 1,2-Diaminocyclohexane," J. Am. Chem. Soc., vol. 113, No. 18, pp. 7063-7064, (1991).
Kagan, et al., "Asymmetric Epoxidation of Simple Olefins with an Optically Active Molybdenum (VI) Peroxo Complex", Angew. Chem. Int. Ed. Engl. vol. 18, No. 6, pp. 485-486, (1979).
Kanatomi et al., "The Dehydrogenation of Nickel(II) Chelates of rac-and meso-2,2'-[1,2,-Diphenylethylene)bis(iminomethylene)]diphenol and Related Compounds," Chem. Soc. of Japan Bull., vol. 56, No. 1, pp. 99-104, (1983).
Katsuki, T. "The First Practical Method for Asymmetric Epoxidation", J. Am. Chem. Soc., vol. 102, No. 18, pp. 5974-5976, (1980).
Kinneary, et al., "Alkene Epoxidation Using Ni(II) Complexes of Chiral Cyclams," Tetra. Lett., vol. 29, No. 8, pp. 877-880, (1988).
Koola, et al., "Cobalt-Catalyzed Epoxidation of Olefins. Dual Pathways for Oxygen Atom Transfer", J. Org. Chem., vol. 52, No. 20, pp. 4545-4553, (1987).
Lecas, A., "Synthese de la Meso-.alpha. .beta. Bis(Diamino-2, 6 Phenyl) Octamethyl Porphyrine", Tetra. Lett., vol. 25, No. 15, pp. 1563-1566, (1984).
Lee, et al., "Enantiomerically Pure Epoxychyomans via Asymmetric Catalysis", Tetrahedron Letters, vol. 32, No. 38, pp. 5055-5058, 1991.
Lee, et al., "Enantiose
Deng Li
Jacobsen Eric N.
Zhang Wei
Nazario-Gonzalez Porfirio
Research Corporation Technologies Inc.
LandOfFree
Chiral catalysts and epoxidation reactions does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Chiral catalysts and epoxidation reactions, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chiral catalysts and epoxidation reactions will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-310134