Patents by Inventor Xumu Zhang

Xumu Zhang has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 7153809
    Abstract: Chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. Processes for the preparation of the ligands are also described.
    Type: Grant
    Filed: January 7, 2005
    Date of Patent: December 26, 2006
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Wenjun Tang
  • Patent number: 7105702
    Abstract: Chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. Processes for the preparation of the ligands are also described.
    Type: Grant
    Filed: November 8, 2002
    Date of Patent: September 12, 2006
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Wenjun Tang
  • Publication number: 20060047128
    Abstract: The present invention provides a chiral ligand, represented by a formula or its enantiomer: X and X? can be independently O, NH, NR, NCOR or S; each of Z1-Z7 and Z1?-Z7? can be independently H, alkyl, aryl, substituted alkyl, substituted aryl, alkoxyl, aryloxyl, nitro, amide, aryoxide, halide, hydroxyl, carboxylate, hetereoaryl, or a cyclic alkene, fused aryl, or cyclic ether group formed from any two adjacent Z groups or any two adjacent Z? groups; Y and Y? can be independently OH, OR, NH2, NHR, NR2, SH, PR2, OPR2, NHPR2, OP(OR)2, COOH, COOR, CONHR, or a linking group formed from Y and Y? groups together. Processes of preparing these ligands, catalysts that employ them and methods of using the catalysts are also provided.
    Type: Application
    Filed: September 1, 2005
    Publication date: March 2, 2006
    Inventor: Xumu Zhang
  • Patent number: 6969694
    Abstract: Chiral ligands and transition metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The chiral ligands include (R,S,S,R)-DIOP*. The ruthenium complex reduces enamide to the corresponding amine with up to 99% enantioselectivity. The transition metal complexes of the chiral ligands are useful in asymmetric reactions such as asymmetric hydrogenation, hydride transfer, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, hydrocarboxylation, isomerization, allylic alkylation, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition and epoxidation reactions. The chiral ligands are of the formula the identittes of the R, R? and Y groups are defined herein.
    Type: Grant
    Filed: February 10, 2004
    Date of Patent: November 29, 2005
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Patent number: 6946569
    Abstract: Chiral phosphine ligands derived from chiral natural products including D-mannitol and tartaric acid. The ligands contain one or more 5-membered phospholane rings with multiple chiral centers, and provide high stereoselectivity in asymmetric reactions.
    Type: Grant
    Filed: March 2, 2004
    Date of Patent: September 20, 2005
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Publication number: 20050159604
    Abstract: A process for preparing a non-racemic aminoalcohol is provided. The process includes the step of contacting a chiral alpha-amino carbonyl compound and hydrogen, in the presence of a non-racemic hydrogenation catalyst, at a temperature, pressure and for a length of time sufficient to produce the non-racemic aminoalcohol. In a preferred embodiment, the process can be described by the reaction scheme: where R is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl or hetereoaryl group; and E can be hydrogen, COOR, CONHR, CONR2, COOH, COR, CN, NO2, alkyl, substituted alkyl, aryl, substituted aryl or hetereoaryl group.
    Type: Application
    Filed: January 14, 2005
    Publication date: July 21, 2005
    Inventor: Xumu Zhang
  • Publication number: 20050137403
    Abstract: A chiral ligand represented by the formula and its enantiomer: wherein A, X, Y and Z are as defined in the specification is provided. Also provided is a process of making the chiral ligands and catalysts prepared from these ligands and a transition metal, a salt thereof or a complex thereof. In addition, a method of preparing an asymmetric compound by a transition metal catalyzed asymmetric reaction, such as, hydrogenation, hydride transfer reaction, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, hydrocarboxylation, allylic alkylation, epoxidation, cyclopropanation, Diels-Alder reaction, Aldol reaction, ene reaction, Heck reaction and Michael addition is provided.
    Type: Application
    Filed: December 17, 2004
    Publication date: June 23, 2005
    Inventors: Xumu Zhang, Duan Liu
  • Publication number: 20050119495
    Abstract: Chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. Processes for the preparation of the ligands are also described.
    Type: Application
    Filed: January 7, 2005
    Publication date: June 2, 2005
    Inventors: Xumu Zhang, Wenjun Tang
  • Patent number: 6855657
    Abstract: 3,3?-Substituted chiral biaryl phosphine and phosphinite ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition, epoxidation, kinetic resolution and [m+n] cycloaddition. The metal complexes are particularly effective in Ru-catalyzed asymmetric hydrogenation of beta-ketoesters to beta-hydroxyesters and Ru-catalyzed asymmetric hydrogenation of enamides to beta amino acids.
    Type: Grant
    Filed: September 11, 2003
    Date of Patent: February 15, 2005
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Patent number: 6828271
    Abstract: Chiral ligands and transition metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The chiral ligands include phospholanes, P,N ligands, N,N ligands, biphenols, and chelating phosphines. The ferrocene-based irridium (R,R)-f-binaphane complex reduces imines to the corresponding amines with 95-99.6% enantioselectivity and reduces &bgr;-substituted-&agr;-arylenamides with 95% enantioselectivity. The transition metal complexes of the chiral ligands are useful in asymmetric reactions such as asymmetric hydrogenation of imines, asymmetric hydride transfer reactions, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, allylic alkylation, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition and epoxidation reactions.
    Type: Grant
    Filed: December 13, 2002
    Date of Patent: December 7, 2004
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Dengming Xiao
  • Publication number: 20040242889
    Abstract: Cyclic &bgr;-(acylamino)acrylate derivatives were hydrogenated using Ru-chiral phosphine ligand catalysts and thereafter converted to the corresponding cyclic &bgr;-aminoacids in high yield and enantioselectivity according to the reaction scheme: 1
    Type: Application
    Filed: May 27, 2004
    Publication date: December 2, 2004
    Applicant: The Penn State Research Foundation
    Inventors: Xumu Zhang, Wenjun Tang
  • Publication number: 20040229846
    Abstract: Chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. Processes for the preparation of the ligands are also described.
    Type: Application
    Filed: May 28, 2004
    Publication date: November 18, 2004
    Applicant: The Penn State Research Foundation
    Inventors: Xumu Zhang, Wenjun Tang
  • Publication number: 20040176618
    Abstract: Chiral phosphine ligands derived from chiral natural products including D-mannitol and tartaric acid. The ligands contain one or more 5-membered phospholane rings with multiple chiral centers, and provide high stereoselectivity in asymmetric reactions.
    Type: Application
    Filed: March 2, 2004
    Publication date: September 9, 2004
    Applicant: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Publication number: 20040167339
    Abstract: Chiral ligands and transition metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The chiral ligands include (R,S,S,R)-DIOP*. The ruthenium complex reduces enamide to the corresponding amine with up to 99% enantioselectivity. The transition metal complexes of the chiral ligands are useful in asymmetric reactions such as asymmetric hydrogenation, hydride transfer, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, hydrocarboxylation, isomerization, allylic alkylation, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition and epoxidation reactions.
    Type: Application
    Filed: February 10, 2004
    Publication date: August 26, 2004
    Applicant: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Publication number: 20040147762
    Abstract: Processes for the preparation of compounds having a chiral carbon substituted with an amine are disclosed. The processes include admixing a ketone with an amine in the presence of a catalyst having a chiral phosphine ligand and an acid. The admixture can also contain a reducing additive. The admixture is then exposed to hydrogen to directly and asymmetrically aminate the ketone.
    Type: Application
    Filed: November 5, 2003
    Publication date: July 29, 2004
    Inventor: Xumu Zhang
  • Patent number: 6727377
    Abstract: Chiral phosphine ligands derived from chiral natural products including D-mannitol and tartaric acid. The ligands contain one or more 5-membered phospholane rings with multiple chiral centers, and provide high stereoselectivity in asymmetric reactions.
    Type: Grant
    Filed: November 6, 2001
    Date of Patent: April 27, 2004
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Publication number: 20040072680
    Abstract: Chiral phospholanes having biaryl chirality for applications in asymmetric catalysis are provided. A series of new chiral mono- or bidentate phosphorus ligands were efficiently prepared through a key intermediate (S)-4-chloro-4,5-dihydro-3H-4-phospha-cyclohepta[2,1-a;3,4-a′]binaphthalene and its derivatives. These ligands were complexed with transition metals to prepare catalysts, which were used in asymmetric catalytic reactions, such as, asymmetric hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution or [m+n] cycloaddition wherein m=3 to 6 and n=2.
    Type: Application
    Filed: April 25, 2003
    Publication date: April 15, 2004
    Applicant: THE PENN STATE RESEARCH FOUNDATION
    Inventor: Xumu Zhang
  • Patent number: 6686428
    Abstract: Compositions and processes of forming chemical bonds, such as carbon-carbon and carbon-heteroatom bonds are provided. The compositions include at least one &agr;-halo carbonyl compound, and one or more transmetallation reagents. The transmetallation reagents are formed by the addition of a metal or metal catalyst to a target compound. The target compound is the compound undergoing chemical bond formation. Bond formation can be carried out in both intermolecular reactions (i.e. between two or more target compounds), or intramolecular (within the same target compound) reactions.
    Type: Grant
    Filed: March 29, 2002
    Date of Patent: February 3, 2004
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Aiwen Lei
  • Publication number: 20030232991
    Abstract: Chiral ligands and transition metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The chiral ligands include (R,S,S,R)-DIOP*. The ruthenium complex reduces enamide to the corresponding amine with up to 99% enantioselectivity. The transition metal complexes of the chiral ligands are useful in asymmetric reactions such as asymmetric hydrogenation, hydride transfer, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, hydrocarboxylation, isomerization, allylic alkylation, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition and epoxidation reactions.
    Type: Application
    Filed: April 10, 2003
    Publication date: December 18, 2003
    Applicant: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Patent number: 6653485
    Abstract: 3,3′-Substituted chiral biaryl phosphine and phosphinite ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition, epoxidation, kinetic resolution and [m+n] cycloaddition. The metal complexes are particularly effective in Ru-catalyzed asymmetric hydrogenation of beta-ketoesters to beta-hydroxyesters and Ru-catalyzed asymmetric hydrogenation of enamides to beta amino acids.
    Type: Grant
    Filed: November 16, 2001
    Date of Patent: November 25, 2003
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang