# US 2014/0155643 A1 · Dirhodium catalyst compositions and synthetic processes related thereto > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0155643 A1 - Document ID: US20140155643A1 - Status: Published application - Kind: A1 - Application number: 14/123,389 - Filed: 2012-06-01 - Published: 2014-06-05 - Earliest claimed: 2011-06-03 - Assignees: Emory University - Applicants: Emory University - Inventors: Huw M. L. Davies; Jørn H. Hansen; Changming Qin - Web page: https://patentgrep.com/patent/US20140155643A1 ## CPC - C07F 15/0073: {Rhodium compounds} - B01J 31/2239: {Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands} - C07F 15/008: {without a metal-carbon linkage} - B01J 2231/325: Cyclopropanations - B01J 2531/0219: Bimetallic complexes, i.e. comprising one or more units of two metals, with metal-metal bonds but no all-metal (M)n rings, e.g. Cr2(OAc)4 - B01J 2531/822: Rhodium - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS ## Abstract This disclosure relates to compositions comprising dirhodium catalysts and uses related thereto, e.g., in enantioselective transformations of donor/acceptor carbenoids. In certain embodiments, the dirhodium catalyst comprises a cyclopropyl ring substituted with a carboxylic acid ligand. In certain embodiments, the disclosure relates to compositions comprising a compound of the following formula, or salts thereof wherein, R1, R2, and R3 are defined herein. ## Claims ### Claim 1 A dirhodium catalyst comprising a cyclopropyl ring substituted with a carboxylic acid ligand. ### Claim 2 A composition comprising a compound of the following formula, or salts thereof wherein, R1 is hydrogen, alkyl, halogen, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkanoyl, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R1 is optionally substituted with one or more, the same or different, R4; R2 is hydrogen, alkyl, halogen, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkanoyl, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R2 is optionally substituted with one or more, the same or different, R4; R3 is hydrogen, alkyl, halogen, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkanoyl, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R3 is optionally substituted with one or more, the same or different, R4; R4 is alkyl, halogen, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkanoyl, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R4 is optionally substituted with one or more, the same or different, R5; R5 is alkyl, halogen, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkanoyl, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R5 is optionally substituted with one or more, the same or different, R6; and R6 is halogen, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, formyl, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, mesyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamoyl, N-ethylsulfamoyl, N,N-dimethylsulfamoyl, N,N-diethylsulfamoyl, N-methyl-N-ethylsulfamoyl, carbocyclyl, aryl, or heterocyclyl. ### Claim 3 (depends on 2) The composition of claim 2, wherein R1 is carbocyclyl, aryl, or heterocyclyl. ### Claim 4 (depends on 2) The composition of claim 2, wherein R1 is an aryl or an aromatic heterocyclyl. ### Claim 5 (depends on 2) The composition of claim 2, wherein R1 is a phenyl optionally substituted with one or more R4. ### Claim 6 (depends on 2) The composition of claim 2, wherein R1 is a phenyl optionally substituted with one or more halogen, alkyl, or alkoxy. ### Claim 7 (depends on 2) The composition of claim 2, wherein R2 is carbocyclyl, aryl, or heterocyclyl. ### Claim 8 (depends on 2) The composition of claim 2, wherein R2 is an aryl or an aromatic heterocyclyl. ### Claim 9 (depends on 2) The composition of claim 2, wherein R2 is a phenyl optionally substituted with one or more R4. ### Claim 10 (depends on 2) The composition of claim 2, wherein R2 is a phenyl optionally substituted with one or more halogen, alkyl, or alkoxy. ### Claim 11 (depends on 2) The composition of claim 2, wherein R3 is carbocyclyl, aryl, or heterocyclyl. ### Claim 12 (depends on 2) The composition of claim 2, wherein R3 is an aryl or an aromatic heterocyclyl. ### Claim 13 (depends on 2) The composition of claim 2, wherein R3 is a phenyl optionally substituted with one or more R4. ### Claim 14 (depends on 2) The composition of claim 2, wherein R3 is a phenyl optionally substituted with one or more halogen, alkyl, or alkoxy. ### Claim 15 (depends on 2) The composition of claim 2, wherein R3 is a phenyl substituted with a halogen. ### Claim 16 (depends on 2) The composition of claim 2, wherein R3 is a phenyl substituted with a halogen in the otho or para position. ### Claim 17 A composition comprising a compound, wherein X is an electron withdrawing group. ### Claim 18 (depends on 17) The composition of claim 17, wherein X is a halogen. ### Claim 19 A composition comprising a compound ### Claim 20 (depends on 1) A method of making a synthetic compound comprising mixing a) a diazo compound, b) a compound with a carbon hydrogen bond, and c) a compound comprising a compound as in claim 1, under conditions such that a synthetic compound is formed comprising a carbon to carbon bond between the diazo compound and the compound with a carbon hydrogen bond. ### Claim 21 (depends on 1) A method of making a synthetic compound comprising mixing a) a diazo compound, b) a compound with a nitrogen hydrogen bond, and c) a compound comprising a compound as in claim 1, under conditions such that a synthetic compound is formed comprising a carbon to nitrogen bond between the diazo compound and the compound with a nitrogen hydrogen bond.