78906-03-3Relevant articles and documents
Stereoselective access to functionalized β-γ unsaturated acids
Thibonnet, Jér?me,Abarbri, Mohamed,Parrain, Jean-Luc,Duchêne, Alain
, p. 4433 - 4441 (2003)
Stereoselective synthesis of vinylstannanes bearing a carboxylic acid function was achieved from β-γ alkynoic acids via hydrostannation, stannylcupration or silastannation reactions. Regioselectivity is highly dependent on the nature of the stannylanions used and on protection of the carboxylic acid function.
Chemoselective γ-Oxidation of β,γ-Unsaturated Amides with TEMPO
Heindl, Sebastian,Lemmerer, Miran,Malzer, Nicolas,Matyasovsky, Ján,Maulide, Nuno,Riomet, Margaux
supporting information, p. 19123 - 19127 (2021/07/26)
A chemoselective and robust protocol for the γ-oxidation of β,γ-unsaturated amides is reported. In this method, electrophilic amide activation, in a rare application to unsaturated amides, enables a regioselective reaction with TEMPO resulting in the title products. Radical cyclisation reactions and oxidation of the synthesised products highlight the synthetic utility of the products obtained.
Enantioselective Alkylamination of Unactivated Alkenes under Copper Catalysis
Bai, Zibo,Zhang, Heng,Wang, Hao,Yu, Hanrui,Chen, Gong,He, Gang
, p. 1195 - 1202 (2021/02/05)
An enantioselective addition reaction of various alkyl groups to unactivated internal alkenes under Cu catalysis has been developed. The reaction uses amide-linked aminoquinoline as the directing group, 4-alkyl Hantzsch esters as the donor of alkyl radicals, and rarely used biaryl diphosphine oxide as a chiral ligand. β-lactams featuring two contiguous stereocenters at Cβ and the β substituent can be obtained in good yield with excellent enantioselectivity. Mechanistic studies indicate that a nucleophilic addition of the alkyl radical to CuII-coordinated alkene is the enantio-determining step.
Manganese-Catalyzed Hydroarylation of Unactivated Alkenes
Liu, Ting,Wang, Congyang,Yang, Yunhui
supporting information, p. 14256 - 14260 (2020/07/13)
Transition-metal-catalyzed hydroarylation of unactivated alkenes with strategic use of remote coordinating functional groups has received significant attention recently to address the issues of both low reactivity and poor selectivity. The bidentate 8-aminoquinoline amide group is the most successfully adopted in unactivated alkenes for Pd and Ni catalysis. We describe the first manganese-catalyzed hydroarylation of unactivated alkenes bearing diverse simple functionalities with arylboronic acids. A series of δ- and γ-arylated amides, ketones, pyridines, and amines was accessed with excellent regioselectivity and in high yields. Hydroalkenylation of unactivated alkenes was also shown to be applicable under this manganese-catalysis regime. The method features earth-abundant manganese catalysis, easily available substrates, broad functional-group tolerance, and excellent regioselective control.
Selective α,δ-hydrocarboxylation of conjugated dienes utilizing CO2and electrosynthesis
Buckley, Benjamin R.,Elmorsy, Saad S.,Malkov, Andrei V.,Mashaly, Mohammad A.,Said, Samy B.,Sheta, Ahmed M.
, p. 9109 - 9114 (2020/09/17)
To date the majority of diene carboxylation processes afford the α,δ-dicarboxylated product, the selective mono-carboxylation of dienes is a significant challenge and the major product reported under transition metal catalysis arises from carboxylation at the α-carbon. Herein we report a new electrosynthetic approach, that does not rely on a sacrificial electrode, the reported method allows unprecedented direct access to carboxylic acids derived from dienes at the δ-position. In addition, the α,δ-dicarboxylic acid or the α,δ-reduced alkene can be easily accessed by simple modification of the reaction conditions. This journal is
Palladium-Catalyzed Amide-Directed Enantioselective Hydrocarbofunctionalization of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand
Wang, Hao,Bai, Zibo,Jiao, Tangqian,Deng, Zhiqiang,Tong, Huarong,He, Gang,Peng, Qian,Chen, Gong
supporting information, p. 3542 - 3546 (2018/03/21)
A Pd-catalyzed amide-directed enantioselective hydrocarbofunctionalization of unactivated alkenes with C-H nucleophiles has been developed using a chiral monodentate oxazoline (MOXin) ligand. Various indoles react at C3 position with aminoquinoline-coupled 3-alkenamides to give γ addition products in good to excellent yield and enantioselectivity. This study represents an important advance of the development of chiral monodentate oxazoline ligands, which have been underexplored for asymmetric catalysis.
A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization
Kawamata, Yu,Hashimoto, Takuya,Maruoka, Keiji
supporting information, p. 5206 - 5209 (2016/05/19)
Chiral electrophilic selenium catalysts have been applied to catalytic asymmetric transformations of alkenes over the past two decades. However, highly enantioselective reactions with a broad substrate scope have not yet been developed. We report the first successful example of this reaction employing a catalyst based on a rigid indanol scaffold, which can be easily synthesized from a commercially available indanone. The reaction efficiently converts β,γ-unsaturated carboxylic acids into various enantioenriched γ-butenolides under mild conditions.
SULFAMATE DERIVATIVE COMPOUND FOR USE IN PREVENTING OR TREATING EPILEPSY
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Page/Page column 123; 124, (2015/06/25)
The present invention relates to a pharmaceutical composition for treating or preventing epilepsy containing a sulfamate derivative compound and/or pharmaceutically acceptable salt thereof as an active ingredient. Furthermore, the present invention relates to a method for treatment or prevention epilepsy comprising administering a sulfamate derivative compound in a pharmaceutically effective amount to a subject in need of treatment or prevention of epilepsy.
A clean and selective radical homocoupling employing carboxylic acids with titania photoredox catalysis
Manley, David W.,Walton, John C.
supporting information, p. 5394 - 5397 (2015/02/19)
A titania photoredox catalysis protocol was developed for the homocoupling of C-centered radicals derived from carboxylic acids. Intermolecular reactions were generally efficient and selective, furnishing the desired dimers in good yields under mild neutral conditions. Selective cross-coupling with two acids proved unsuccessful. An intra-molecular adaptation enabled macrocycles to be prepared, albeit in modest yields. (Chemical Equation Presented).
Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids
Morrill, Louis C.,Smith, Samuel M.,Slawin, Alexandra M. Z.,Smith, Andrew D.
, p. 1640 - 1655 (2014/03/21)
Isothiourea HBTM-2.1 promotes the catalytic asymmetric α- functionalization of 3-alkenoic acids through formal [2 + 2] cycloadditions with N-tosyl aldimines and formal [4 + 2] cycloadditions with either 4-aryltrifluoromethyl enones or N-aryl-N-aroyl diazenes, providing useful synthetic building blocks in good yield and with excellent enantiocontrol (up to >99% ee). Stereodefined products are amenable to further synthetic elaboration through manipulation of the olefinic functionality.
