13048-81-2Relevant academic research and scientific papers
The synergistic copper/ppm Pd-catalyzed hydrocarboxylation of alkynes with formic acid as a CO surrogate as well as a hydrogen source: An alternative indirect utilization of CO2
Chen, Kai-Hong,He, Liang-Nian,Qiu, Li-Qi,Xia, Shu-Mei,Yang, Zhi-Wen,Yao, Xiang-Yang
supporting information, p. 8089 - 8095 (2021/11/01)
An unprecedented strategy has been developed involving the earth-abundant Cu-catalyzed hydrocarboxylation of alkynes with HCOOH to (E)-acrylic derivatives with high regio- and stereoselectivity via synergistic effects with ppm levels of a Pd catalyst. Both symmetrical and unsymmetrical alkynes bearing various functional groups were successfully hydrocarboxylated with HCOOH, and the modification of a pharmaceutical molecule exemplified the practicability of this process. This protocol employs HCOOH as both a CO surrogate and hydrogen donor with 100% atom economy and it can be viewed as an alternative approach for indirect CO2 utilization. Mechanistic investigations indicate a Cu/ppm Pd cooperative catalysis mechanism via alkenylcopper species as potential intermediates formed from Cu-hydride active catalytic species with HCOOH as a hydrogen source. This bimetallic system involving inexpensive Cu and trace Pd provides a reliable and efficient hydrocarboxylation method to access industrially useful acrylic derivatives with HCOOH as a hydrogen source, and it provides novel clues for optimizing other Cu-H-related co-catalytic systems.
Copper-Photocatalyzed Contra-Thermodynamic Isomerization of Polarized Alkenes
Bouillon, Jean-Philippe,Brégent, Thibaud,Poisson, Thomas
, p. 7688 - 7693 (2020/10/09)
The contra-thermodynamic isomerization of α- and β-substituted cinnamate derivatives catalyzed by the Cu(OAc)2/rac-BINAP complex under blue light irradiation is reported. The use of an oxazolidinone template, which favored the complexation of the copper catalyst to the substrate, allowed the E → Z isomerization of the catalytically formed chromophore under simple and robust reaction conditions in good to excellent ratios. The mechanism of this process based on the transient formation of a chromophore was also studied.
Macrolide Synthesis through Intramolecular Oxidative Cross-Coupling of Alkenes
Jiang, Bing,Zhao, Meng,Li, Shu-Sen,Xu, Yun-He,Loh, Teck-Peng
, p. 555 - 559 (2018/02/21)
A RhIII-catalyzed intramolecular oxidative cross-coupling between double bonds for the synthesis of macrolides is described. Under the optimized reaction conditions, macrocycles containing a diene moiety can be formed in reasonable yields and with excellent chemo- and stereoselectivity. This method provides an efficient approach to synthesize macrocyclic compounds containing a 1,3-conjugated diene structure.
Enantioselective Cobalt-Catalyzed Sequential Nazarov Cyclization/Electrophilic Fluorination: Access to Chiral α-Fluorocyclopentenones
Zhang, Heyi,Cheng, Biao,Lu, Zhan
supporting information, p. 4028 - 4031 (2018/07/15)
A newly designed thiazoline iminopyridine ligand for enantioselective cobalt-catalyzed sequential Nazarov cyclization/electrophilic fluorination was developed. Various chiral α-fluorocyclopentenones were prepared with good yields and diastereo- and enantioselectivities. Further derivatizations could be easily carried out to provide chiral cyclopentenols with three contiguous stereocenters. Furthermore, a direct deesterification of fluorinated products could afford chiral α-single fluorine-substituted cyclopentenones.
DERIVATIVES OF SULINDAC CAN PROTECT NORMAL CELLS AGAINST OXIDATIVE DAMAGE
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Page/Page column 34, (2018/10/19)
The disclosure provides chemical compounds possessing therapeutic and/or protective properties against oxidative damage. Methods of making such therapeutic and/or protective compounds and associated compositions are also provided, as are methods for their use, which include protecting cells from oxidative damage and/or inhibiting production of ROS in a cell or subject, as well as preventing or reducing the extent of tissue damage caused by an ischemic event in a subject at elevated risk of such an event.
INDENYL COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND MEDICAL USES THEREOF
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Paragraph 0264, (2016/07/05)
Disclosed are compounds, for example, compounds of formula I, wherein R, R0, R1-R8, n, X, Y, Y′, and E are as described herein, pharmaceutical compositions containing such compounds, and methods of treating or preventing a disease or condition, for example, cancer.
METHOD OF TREATING OR PREVENTING RAS-MEDIATED DISEASES
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Paragraph 0261, (2016/07/05)
Disclosed are compounds, for example, a compound of formula I, wherein R, R0, R1-R8, n, X, Y, Y′, and E are as described herein, pharmaceutical compositions containing such compounds, and methods of treating or preventing a disease or condition for example, cancer, mediated by the ras gene.
A practical, enantioselective synthesis of the fragrances canthoxal and silvial, and evaluation of their olfactory activity
Beghetto, Valentina,Scrivanti, Alberto,Bertoldini, Matteo,Aversa, Manuela,Zancanaro, Aurora,Matteoli, Ugo
, p. 272 - 278 (2015/05/05)
The fragrances (S)-(+)- and (R)-(-)-canthoxal [(S)-(+)- and (R)-(-)-3-(4-methoxyphenyl)-2-methylpropanal] and (+)- and (-)-Silvial [(+)- and (-)-3-(4-isobutylphenyl)-2-methylpropanal] have been synthesized in high enantiopurity via a simple fou
Synthesis of chiral α-benzyl-β2-hydroxy carboxylic acids through iridium-catalyzed asymmetric hydrogenation of α- oxymethylcinnamic acids
Li, Ze-Yu,Song, Song,Zhu, Shou-Fei,Guo, Na,Wang, Li-Xin,Zhou, Qi-Lin
supporting information, p. 783 - 787 (2014/10/16)
An asymmetric hydrogenation of α-oxymethylcinnamic acids was developed by using chiral spiro phosphine-oxazoline/iridium complexes as catalysts to prepare β2-hydroxycarboxylic acids with high reactivity (TON up to 2000) and excellent enantioselectivity (up to 99.5% ee). By using this highly efficient asymmetric hydrogenation as a key step, a concise total synthesis of natural product homoisoflavone (S)-(+)-4 was accomplished. An asymmetric hydrogenation of α-oxymethylcinnamic acids was developed to prepare β2-hydroxycarboxylic acids with high reactivity (TON up to 2000) and excellent enantioselectivity (up to 99.5% ee), which was applied to a concise total synthesis of a natural product homoisoflavone. Copyright
Microwave-assisted synthesis of the (E)-α-methylalkenoate framework from multifunctionalized allylic phosphonium salts
Meier, Lidiane,Ferreira, Misael,Sa, Marcus M.
, p. 179 - 186 (2012/07/14)
A convenient and general microwave-assisted method for the synthesis of stereochemically defined α-methylalkenoic acids and esters from allylic phosphonium salts in a basic aqueous medium is described. A selective preparation of acids or esters was dependent on the base (NaOH or NaHCO 3) employed in the reaction and could be achieved with good to excellent yields under mild conditions in the absence of hydrides and reducing agents.
