- Myoglobin-catalyzed intermolecular carbene N-H insertion with arylamine substrates
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Engineered variants of the heme-containing protein myoglobin can efficiently catalyze the insertion of α-diazo esters into the N-H bond of arylamines, featuring a combination of high chemoselectivity, elevated turnover numbers, and broad substrate scope.
- Sreenilayam, Gopeekrishnan,Fasan, Rudi
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Read Online
- Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams
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A visible-light photoredox-catalyzed reductive α-aminomethyl carboxylation of styrenes with sodium glycinates and CO2 has been developed to synthesize a series of α,α-disubstituted γ-amino acids and γ-lactams with high efficiency and regioselectivity. Notably, CO2 released from the decarboxylation step can be reused for the subsequent carboxylation. Distinct from the previous reactions with the same type of substrates leading to simple decarboxylation and olefin hydroalkylation, this process involves additional CO2 sequestration, thus leading to olefin α-aminomethyl carboxylation. These findings not only provide new access to α,α-disubstituted γ-amino acids and γ-lactams but also serve as a proof of concept for CO2 reutilization in decarboxylation reactions.
- Zhou, Cong,Li, Miao,Sun, Jianwei,Cheng, Jiang,Sun, Song
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supporting information
p. 2895 - 2899
(2021/05/05)
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- Exploiting Synergistic Catalysis for an Ambient Temperature Photocycloaddition to Pyrazoles
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Sydnone-based cycloaddition reactions are a versatile platform for pyrazole synthesis, however they operate under harsh conditions (high temperature and long reaction times). Herein we report a strategy that addresses this limitation utilizing the synergistic combination of organocatalysis and visible-light photocatalysis. This new approach proceeds under ambient conditions and with excellent levels of regiocontrol. Mechanistic studies suggest that photoactivation of sydnones, rather than enamines, is key to the successful implementation of this process.
- Lakeland, Christopher P.,Watson, David W.,Harrity, Joseph P. A.
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supporting information
p. 155 - 159
(2019/12/11)
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- FERROCHELATASE INHIBITORS AND METHODS OF USE
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The invention relates to a method of treatment of a patient with a ferrochelatase inhibitor, or a pharmaceutically acceptable salt thereof, or a derivative thereof. Also, the invention relates to a method of treatment of a patient with a ferrochelatase in
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Page/Page column 57; 58
(2019/11/19)
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- CATHEPSIN-D AND ANGIOGENESIS INHIBITORS AND COMPOSITIONS THEREOF FOR TREATING BREAST CANCER
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The invention relates to Cathepsin-D and angiogenesis inhibitors and compositions thereof for treating breast cancer. More particularly, the invention relates to the design and synthesis of inhibitors of Cathepsin D which exhibits antiproliferative activity and also inhibits angiogenesis. The present invention also relates to the compositions thereof for treating breast cancer.
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Page/Page column 18
(2018/09/28)
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- Functionalization of N-arylglycine esters: Electrocatalytic access to C-C bonds mediated by n-Bu4NI
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An efficient electrocatalytic functionalization of N-arylglycine esters is reported. The protocol proceeds in an undivided cell under constant current conditions employing the simple, cheap and readily available n-Bu4NI as the mediator. In addition, it is demonstrated that the mediated process is superior to the direct electrochemical functionalization.
- Luo, Mi-Hai,Jiang, Yang-Ye,Xu, Kun,Liu, Yong-Guo,Sun, Bao-Guo,Zeng, Cheng-Chu
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supporting information
p. 499 - 505
(2018/03/21)
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- Copper Triflate Catalyzed Oxidative α-Allylation of Glycine Derivatives
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Copper triflate catalyzed oxidative C-H functionalization of glycine derivatives with allyltributyltin has been established using oxygen or tert -butyl hydroperoxide as oxidant. Various glycine esters and glycine amides were suitable substrates for this oxidative allylation reaction and afforded the desired homoallylic amines in moderate to good yields.
- Chen, Ting-Ting,Cai, Chun
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supporting information
p. 1368 - 1372
(2017/06/27)
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- MYOGLOBIN-BASED CATALYSTS FOR CARBENE TRANSFER REACTIONS
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Methods are provided for carrying out carbene transfer transformations such as olefin cyclopropanation reactions, carbene heteroatom-H insertion reactions (heteroatom = N, S, Si), sigmatropic rearrangement reactions, and aldehyde olefination reactions with high efficiency and selectivity by using a novel class of myoglobin-based biocatalysts. These methods are useful for the synthesis of a variety of organic compounds which contain one or more new carbon-carbon or carbon-heteroatom (N, S, or Si) bond. The methods can be applied for conducting these transformations in vitro (i.e., using the biocatalyst in isolated form) and in vivo (i.e., using the biocatalyst in a whole cell system).
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Paragraph 0071; 00266
(2016/06/14)
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- Iron-catalyzed oxidative tandem reactions with TEMPO oxoammonium salts: Synthesis of dihydroquinazolines and quinolines
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A straightforward iron-catalyzed divergent oxidative tandem synthesis of dihydroquinazolines and quinolines from N-alkylanilines using a TEMPO oxoammonium salt as a mild and nontoxic oxidant has been developed. Fe(OTf) 2 was the Lewis acid cata
- Rohlmann, Renate,Stopka, Tobias,Richter, Heinrich,Garcia Mancheno, Olga
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p. 6050 - 6064
(2013/07/26)
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- Cross-dehydrogenative coupling reactions by transition-metal and aminocatalysis for the synthesis of amino acid derivatives
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The direct approach: The title coupling reactions of N-aryl glycine esters with unmodified ketones occurred smoothly in the presence of tert-butyl hydroperoxide (TBHP) or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under mild conditions (see scheme). The oxidant used for C-H activation determined the selectivity of the reactions for a particular type of ketone substrate. Copyright
- Xie, Jin,Huang, Zhi-Zhen
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supporting information; experimental part
p. 10181 - 10185
(2011/02/27)
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- beta -thiopropionyl-aminoacid derivatives and their use as beta -lactamase inhibitors
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PCT No. PCT/EP97/00516 Sec. 371 Date Jan. 13, 1999 Sec. 102(e) Date Jan. 13, 1999 PCT Filed Feb. 3, 1997 PCT Pub. No. WO97/30027 PCT Pub. Date Aug. 21, 1997A method of treatment of bacterial infections in humans or animals which comprises administering, in combination with a beta -lactam antibiotic, a therapeutically effective amount of an amino acid derivative of Formula (I) or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof, wherein: R is hydrogen, a salt forming cation or an in vivo hydrolysable ester-forming group; R1 is hydrogen, (C1-6)alkyl optionally substituted by up to three halogen atoms or by a mercapto, (C1-6)alkoxy, hydroxy, amino, nitro, carboxy, (C1-6)alkylcarbonyloxy, (C1-6)alkoxycarbonyl, formyl or (C1-6)alkylcarbonyl group, (C3-7)cycloalkyl, (C3-7)cycloalkyl(C2-6)alkyl, (C2-6)alkenyl, (C2-6)alkynyl, aryl, aryl(C1-6)alkyl, heterocyclyl or heterocyclyl(C1-6)alkyl; R2 is hydrogen, (C1-6)alkyl or aryl(C1-6)alkyl; R3 is hydrogen, (C1-6)alkyl optionally substituted by up to three halogen atoms, (C3-7)cycloalkyl, fused aryl(C3-7)cycloalkyl, (C3-7)cycloalkyl(C2-6)alkyl, (C2-6)alkenyl, (C2-6)alkynyl, aryl, aryl-(CHR10)m-X-(CHR11)n, heterocyclyl or heterocyclyl-(CHR10)m-X-(CHR11)n, where m is 0 to 3, n is 1 to 3, each R10 and R11 is independently hydrogen or (C1-4)alkyl and X is O, S(O)x where x is 0-2, or a bond; R4 is hydrogen, or an in vivo hydrolysable acyl group; and R5 and R6 are independently hydrogen and (C1-6)alkyl or together represent (CH2)p where p is 2 to 5. Some compounds are claimed per se.
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