The Penn State Research Foundation

Rutgers, the State University of New Jersey

Xumu Zhang

Wenjun Tang

Dengming Xiao

Yongjun Yan

Duan Liu

Aiwen Lei

A ligand having the structure or its enantiomer; (I) wherein: each one of R, R, Rand Ris selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CHNH; *CH(CH)NH(C*,R); and the organocatalyst is an organic molecule catalyst covalently bound to the bridge group. Also, a catalyst having the structure or its enantiomer: (II) wherein: each one of R, R, Rand Ris selected from alkyl, cycloalkyl, and aryl; the bridge group is selected from CHNH; *CH(CH)NH(C*,R); and *CH(CH)NH(C*,S); the organocatalyst is an organic molecule catalyst covalently bound to the bridge group; and M is selected from the group consisting of Rh, Pd, Cu, Ru, Ir, Ag, Au, Zn, Ni, Co, and Fe. 

Metallorganocatalysis for asymmetric transformations

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 Z-Zand Z&#x2032;-Z&#x2032; 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&#x2032; groups; Y and Y&#x2032; can be independently OH, OR, NH, NHR, NR, SH, PR, OPR, NHPR, OP(OR), COOH, COOR, CONHR, or a linking group formed from Y and Y&#x2032; groups together. Processes of preparing these ligands, catalysts that employ them and methods of using the catalysts are also provided.

Chiral spiro compounds and their use in asymmetric catalytic reactions

Phosphine triazole ligand compounds, prepared through click chemistry, complex with transition metals to form transition metal-phosphine triazole ligand complexes. These complexes are useful catalysts in coupling reactions such as Suzuki-Miyaura coupling, Stille coupling, Negishi coupling, Sonagashira coupling, carbon-heteroatom bond-forming reactions (C&#x2014;O and C&#x2014;N), alpha alkylation of carbonyls, Heck coupling reactions, and hydrogenation reactions.

Clickphosphines for transition metal-catalyzed reactions

Tetraphosphorous ligands are combined with transition metal salts to form catalysts for use in hydroformylation, isomerization-hydroformylation, hydrocarboxylation, hydrocyan-ation, isomerization-formylation, hydroaminomethylation and similar related reactions.

Tetraphosphorus ligands for catalytic hydroformylation and related reactions

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 Z-Zand Z&#x2032;-Z&#x2032; can be independently H, alkyl, aryl, substituted alkyl, substituted aryl, alkoxyl, aryloxyl, nitro, amide, aryloxide, halide, hydroxyl, carboxylate, heteroaryl, or a cyclic alkene, fused aryl, or cyclic ether group formed from any two adjacent Z groups or any two adjacent Z&#x2032; groups; Y and Y&#x2032; can be independently OH, OR, NH, NHR, NR, SH, PR, OPR, NHPR, OP(OR), COOH, COOR, CONHR, or a linking group formed from Y and Y&#x2032; groups together. Processes of preparing these ligands, catalysts that employ them and methods of using the catalysts are also provided.

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.

Oxazoline ligands for asymmetric catalysis

Cyclic &#x3b2;-(acylamino)acrylate derivatives were hydrogenated using Ru-chiral phosphine ligand catalysts and thereafter converted to the corresponding cyclic &#x3b2;-aminoacids in high yield and enantioselectivity according to the reaction scheme: 

Preparation of chiral cyclic amino acids and derivatives

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.

P-chiral phospholanes and phosphocyclic compounds and their use in asymmetric catalytic reactions

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 formulathe identittes of the R, R' and Y groups are defined herein.

Chiral phosphines, transition metal complexes thereof and uses thereof in asymmetric reactions

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.

Asymmetric catalysis based on chiral phospholanes and hydroxyl phospholanes

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.

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State College, PA, United States of America

Xumu Zhang