- Photoinduced Hydrocarboxylation via Thiol-Catalyzed Delivery of Formate across Activated Alkenes
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Herein we disclose a new photochemical process to prepare carboxylic acids from formate salts and alkenes. This redox-neutral hydrocarboxylation proceeds in high yields across diverse functionalized alkene substrates with excellent regioselectivity. This operationally simple procedure can be readily scaled in batch at low photocatalyst loading (0.01% photocatalyst). Furthermore, this new reaction can leverage commercially available formate carbon isotologues to enable the direct synthesis of isotopically labeled carboxylic acids. Mechanistic studies support the working model involving a thiol-catalyzed radical chain process wherein the atoms from formate are delivered across the alkene substrate via CO2?- as a key reactive intermediate.
- Alektiar, Sara N.,Wickens, Zachary K.
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supporting information
p. 13022 - 13028
(2021/09/03)
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- Modular 1,1′-Ferrocenediyl-cored P-Stereogenic Diphosphines: ′′JDayPhos′′ Series and its Use in Rhodium(I)-Catalyzed Hydrogenation
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A novel ferrocene-based P-stereogenic diphospine ligand series dubbed JDayPhos was developed, which rhodium(I) complexes of some of its members exhibited excellent enantioselectivity (up to >99% ee) and high activity in asymmetric hydrogenation of β-unsubstituted or -substituted itaconates and α-methylene-γ-oxo-carboxylates. (Figure presented.).
- Poklukar, Ga?per,Stephan, Michel,Mohar, Barbara
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supporting information
p. 2566 - 2570
(2018/05/16)
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- Preparation method of mitiglinide calcium
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The invention relates to a preparation method of mitiglinide calcium, which includes steps of step 1, synthesis of benzal butanedioic acid; step 2, synthesis of benzylsuccinic acid; step 3, synthesisof (S)-benzylsuccinic acid (R)-alpha- phenylethylamine; step 4, synthesis of (S)-benzylsuccinic acid; step 5, synthesis of 2S-dihydro-isoindole indolebutyric acid; step 6, synthesis of crude product of mitiglinide calcium; step 7, refining of mitiglinide calcium.
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- Triflic Acid Mediated Cyclization of Unsymmetrical N -Phenethyl- and N -(3-Indolylethyl)succinimides: Regio- and Diastereoselective Synthesis of Substituted Pyrroloisoquinolinones and Indolizino-indolones
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The regio and diastereoselective synthesis of 1 or 2 alkyl-substituted pyrroloisoquinolinones and indolizinoindolones by triflic acid mediated cyclization via an electrophilic activation of unsymmetrical succinimide carbonyl groups followed by the reducti
- Selvakumar, Jayaraman,Mangalaraj, Selvaraj,Achari, Kamsali Murali Mohan,Mukund, Krishna,Ramanathan, Chinnasamy Ramaraj
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p. 1053 - 1064
(2017/02/24)
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- Decatungstate photocatalyzed benzylation of alkenes with alkylaromatics
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The direct benzylation of electrophilic al-kenes with alkylbenzenes has been achieved by decatungstate photocatalysis in a high ionic strength medium (5:1 acetonitrile/water mixed solvents, 0.5 M lithium perchlorate). The reaction has been extended to ring-substituted (Cl, F, CN) toluenes and further alkylbenzenes. Intramolecular selectivity (p-cymene, 4-methylanisole) and deuteration effects support the atom transfer character of the process that, however, requires a sufficient stabilization of the intermediate polar exciplex to occur. The reactivity of the deca-tungstate anion is compared with that of aromatic ketones, the benchmark of photochemical hydrogen/ electron transfer processes.
- Qrareya, Hisham,Ravelli, Davide,Fagnoni, Maurizio,Albini, Angelo
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supporting information
p. 2891 - 2899
(2014/03/21)
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- Decatungstate as photoredox catalyst: Benzylation of electron-poor olefins
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Excited tetrabutylammonium decatungstate (TBADT), known to activate a variety of compounds via hydrogen atom transfer (HAT), has now been applied as a photoredox catalyst for the effective oxidative cleavage of benzyl silanes and radical benzylation of reducible olefins occurring in isolated yields from poor to excellent.
- Montanaro, Sara,Ravelli, Davide,Merli, Daniele,Fagnoni, Maurizio,Albini, Angelo
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supporting information; experimental part
p. 4218 - 4221
(2012/09/22)
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- 2-Amino-4-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors
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Novel compounds are provided which are glycogen phosphorylase inhibitors which are useful in treating, preventing or slowing the progression of diseases requiring glycogen phosphorylase inhibitor therapy such as diabetes and related conditions (such as hy
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Page/Page column 17
(2010/11/08)
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- Preparation of (R)-(-)- and (S)-(+)-3-hydroxymethyl-1-tetralone tosylates, key intermediates in the synthesis of new CNS drugs, via resolution of precursors
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The preparation of (R)-(-)- and (S)-(+)-3-hydroxymethyl-1-tetralone tosylates, key intermediates in the synthesis of new CNS drugs in the aminobutyrophenone family, has been developed via classical resolutions or lipase-catalyzed kinetic resolution of one of their precursors.
- Caro, Yolanda,Masaguer, Christian F.,Ravina, Enrique
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p. 381 - 387
(2007/10/03)
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- Nitroalkanes and dimethyl maleate as source of 3-alkyl succinic anhydrides and (E)-3-alkylidene succinic anhydrides
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Nitroalkanes react with dimethyl maleate giving a tandem Michael addition/elimination of nitrous acid. The obtained (E)-2-alkylidene dimethyl succinates are: (i) reduced to the corresponding 2-alkyl dimethyl succinates which after hydrolysis produce 1,4-dicarboxylic acids that are prone to convert into the corresponding 3-alkyl succinic anhydrides or (ii) hydrolysed to (E)-2-alkylidene-succinic acids that are easily cyclised to (E)-3-alkylidene succinic anhydrides.
- Ballini, Roberto,Bosica, Giovanna,Fiorini, Dennis,Righi, Paolo
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p. 681 - 685
(2007/10/03)
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- Synthesis of monosubstituted succinic acids from tert-butylsuccinate
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We report the preparation and alkylation of the dianion of t-butylsuccinate. This alkylation reaction has proven to be a useful method for the preparation of monosubstituted succinic acids and anhydrides.
- Bergmeier,Ismail
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p. 1369 - 1371
(2007/10/03)
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- Inhibitors of microsomal triglyceride transfer protein and method
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Compounds are provided which inhibit microsomal triglyceride transfer protein and thus are useful for lowering serum lipids and treating atherosclerosis and related diseases. The compounds have the structure STR1 wherein R1 to R7, Q, X and Y are as defined herein.
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- Nucleic acids encoding microsomal trigyceride transfer protein
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Nucleic acid sequences, particularly DNA sequences, coding for all or part of the high molecular weight subunit of microsomal triglyceride transfer protein, expression vectors containing the DNA sequences, host cells containing the expression vectors, and methods utilizing these materials. The invention also concerns polypeptide molecules comprising all or part of the high molecular weight subunit of microsomal triglyceride transfer protein, and methods for producing these polypeptide molecules. The invention additionally concerns novel methods for preventing, stabilizing or causing regression of atherosclerosis and therapeutic agents having such activity. The invention concerns further novel methods for lowering serum liquid levels and therapeutic agents having such activity.
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- Process for the enantioselective synthesis of 2(R)-benzylsuccinic acid monoamide derivatives
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Two processes are described for the preparation of the optically pure compounds of formula 1: STR1 in which R1 and R2 are e.g. alkyl, R3 and R4 are e.g. hydrogen and R5 is e.g. hydrogen. Both processes include, as key steps, the enantioselective hydrogenation of a C=C double bond and the regioselective formation of a dicarboxylic acid monoamide derivative. In one process a phenylitaconic acid derivative is asymmetrically hydrogenated to give an optically active (R)-benzylsuccinic acid which is then converted to a diester, said diester being converted to the monoamide compound of formula 1. In the second process, a phenylitaconic acid derivative is converted to its anhydride, and the anhydride is then converted to a monoamide which is then asymmetrically hydrogenated to give the compound of formula 1.
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