- Cu(II)-promoted oxidative C-N bond cleavage of N-benzoylamino acids to primary aryl amides
-
A novel protocol for CuCl2-promoted oxidative C-N bond cleavage of N-benzoyl amino acids was developed. It is the first example of using accessible amino acid as an ammonia synthetic equivalent for the synthesis of primary aryl amides via CuCl2-promoted oxidative C-N bond cleavage reaction. The present protocol shows excellent functional group tolerance and provides an alternative method for the synthetic of primary aryl amides in 84-96% yields.
- Zhou, Liandi,Liu, Wei,Zhao, Yongli,Chen, Junmin
-
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- Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds
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A palladium-catalyzed allenamide carbopalladation/allylation with active methine compounds has been developed. Various indoles and isoquinolinones bearing a quaternary carbon center were achieved with good efficiency, a broad substrate scope and good functional group tolerance. This reaction underwent cascade oxidative addition, carbopalladation, and allylic alkylation, and two new C-C bonds were formed in one pot.
- Zhu, Xiaoyi,Li, Ruibo,Yao, Hequan,Lin, Aijun
-
supporting information
p. 4630 - 4634
(2021/06/28)
-
- Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes
-
A nickel-catalyzed, multicomponent regio- and enantioselective coupling via sequential hydroformylation and carbonylation from readily available starting materials has been developed. This modular multicomponent hydrofunctionalization strategy enables the straightforward reductive hydrocarbonylation of a broad range of unactivated alkenes to produce a wide variety of unsymmetrical dialkyl ketones bearing a functionalized α-stereocenter, including enantioenriched chiral α-aryl ketones and α-amino ketones. It uses chiral bisoxazoline as a ligand, silane as a reductant, chloroformate as a safe CO source, and a racemic secondary benzyl chloride or an N-hydroxyphthalimide (NHP) ester of a protected α-amino acid as the alkylation reagent. The benign nature of this process renders this method suitable for late-stage functionalization of complex molecules.
- Chen, Jian,Zhu, Shaolin
-
supporting information
p. 14089 - 14096
(2021/09/13)
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- Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: Access to chiral benzothiazolopyrimidine derivatives
-
An organocatalytic asymmetric domino Mannich/cyclization reaction between 2-benzothiazolimines with azlactones has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20?:?1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers.
- Ni, Qijian,Wang, Xuyang,Xu, Fangfang,Chen, Xiaoyun,Song, Xiaoxiao
-
supporting information
p. 3155 - 3158
(2020/03/23)
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- Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones
-
The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19?:?1 dr. An exploration of the structure of the catalyst bisguanidinium was undertaken, revealing a bifunctional catalytic model.
- Xie, Lihua,Dong, Shunxi,Zhang, Qian,Feng, Xiaoming,Liu, Xiaohua
-
supporting information
p. 87 - 90
(2019/01/03)
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- METHODS OF TREATING OR PREVENTING COGNITIVE IMPAIRMENT USING INDANE ACETIC ACID DERIVATIVES BASED ON APOE4 GENOTYPE
-
The present invention provides indane acetic acid and their derivatives and methods for the treating and/or preventing of cognitive disorders based on the ApoE4 genotype of human subjects.
- -
-
Paragraph 0508-0510
(2018/06/15)
-
- METHODS OF DOSE ADMINISTRATION FOR TREATING OR PREVENTING COGNITIVE IMPAIRMENT USING INDANE ACETIC ACID DERIVATIVES
-
The present invention provides indane acetic acid and their derivatives and methods for the treating and/or preventing of cognitive disorders.
- -
-
Paragraph 0511; 0512
(2018/06/15)
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- Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media
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The kinetics of the reaction of a series of α-amino acids with 4-nitrophenyl acetate, 4-nitrophenyl benzoate, and 2,4,6-trinitrophenyl benzoate in aqueous 1,4-dioxane medium has been studied. Kinetics of the reactions involving 4-nitrophenyl acetate and 2,4,6-trinitrophenyl benzoate has complied with the Br?nsted dependence and revealed linear correlation between rate constant logarithm and the energy difference of the frontier orbitals of α-amino acids anions.
- Kochetova,Kustova,Kuritsyn
-
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- Cu(II)-promoted oxidative C-N bond cleavage of N-benzoylamino acids to primary aryl amides
-
A novel protocol for CuCl2-promoted oxidative C-N bond cleavage of N-benzoyl amino acids was developed. It is the first example of using accessible amino acid as an ammonia synthetic equivalent for the synthesis of primary aryl amides via CuCl2-promoted oxidative C-N bond cleavage reaction. The present protocol shows excellent functional group tolerance and provides an alternative method for the synthetic of primary aryl amides in 84-96percent yields.
- Chen, Junmin,Liu, Wei,Zhao, Yongli,Zhou, Liandi
-
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- Synthesis of an enantiopure thioester as key substrate for screening the sensitivity of penicillin binding proteins to inhibitors
-
The synthesis of the enantiopure thioester (R)-2-(2-benzamidopropanoylthio)acetic acid was developed. After the exploration of several activation methods, reaction conditions were found for the formation of the thioester bond in the presence of propylphosphonic anhydride with high enantioselectivity (ee > 99%). The thioester activity of Penicillin Binding Proteins is helpful in research programs looking for new lead structures to overcome the problem of bacterial resistance.
- Simon, Justine F.,Bouillez, André,Frère, Jean-Marie,Luxen, André,Zervosen, Astrid
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- Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives
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Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.
- Wang, Tianli,Yu, Zhaoyuan,Hoon, Ding Long,Phee, Claire Yan,Lan, Yu,Lu, Yixin
-
supporting information
p. 265 - 271
(2016/01/25)
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- Catalyst-free synthesis of N -(1,7-dioxotetrahydropyrazolo[1,2-a]pyrazol-2- yl)benzamide derivatives by 1,3-dipolar cycloaddition and rearrangement
-
N-(1,7-Dioxotetrahydropyrazolo[1,2-a]pyrazol-2-yl)-benzamide derivatives, a novel class of compounds, were synthesized by 1,3-dipolar cycloaddition of azomethine imines with azlactones and subsequent rearrangement. The reaction can be completed rapidly under mild conditions without a catalyst. Georg Thieme Verlag Stuttgart New York.
- Liu, Wenjing,Xu, Yu,Sun, Xingxia,Lu, Dapeng,Guo, Lijuan
-
supporting information
p. 1093 - 1096
(2014/05/20)
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- Bronsted acid accelerated Pd-catalyzed direct asymmetric allylic alkylation of azlactones with simple allylic alcohols: A practical access to quaternary allylic amino acid derivatives
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A Bronsted acid accelerated Pd-catalyzed asymmetric allylic alkylation of azlactones with simple allylic alcohols under mild reaction conditions has been realized, which provides a direct and readily scalable approach for the synthesis of all-carbon quaternary allylic amino acid derivatives in excellent yields and good enantioselectivities. (Chemical Equation Presented).
- Zhou, Hui,Yang, Huameng,Liu, Muwen,Xia, Chungu,Jiang, Gaoxi
-
supporting information
p. 5350 - 5353
(2015/01/09)
-
- Organocatalyzed asymmetric 1,4-addition of azlactones to α,β-unsaturated trichloromethyl ketones: Synthesis of α,α-disubstituted α-amino acid derivatives
-
The first asymmetric 1,4-addition of azlactones to α,β-unsaturated trichloromethyl ketones catalyzed by cinchona alkaloid derived bifunctional thiourea catalysts was developed. A series of α,α-disubstituted α-amino acid derivatives bearing a quaternary stereocenter at the α-position were obtained in high yields with excellent diastereo- and enantioselectivities (up to -20:1 dr and 99% ee). In addition, the trichloromethyl moiety in these adducts was identified as a good leaving group.
- Zhang, Jinlong,Liu, Xihong,Wu, Chongyang,Zhang, Panpan,Chen, Jianbo,Wang, Rui
-
supporting information
p. 7104 - 7108
(2015/01/16)
-
- Synthesis of di- and tri-substituted imidazole-4-carboxylates via PBu3-mediated [3+2] cycloaddition
-
Some new di- and trisubstituted imidazole-4-carboxylates were prepared from amidoacetic acids 3 in the present report. The key step to establish such imidazole- 4-carboxylates stemmed from the PBu3-mediated [3+2] cycloaddition between in situ-generated Δ2-oxazolinone 4 and ethyl cyanoformate6. Our results indicated that trisubstituted imidazoles 7-20 were afforded in better yields than those of disubstituted imidazoles 21-27. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Hsu, Mei-Yuan,Dietrich, Justin,Hulme, Christopher,Shaw, Arthur Y.
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p. 1538 - 1542
(2013/05/21)
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- Synthesis and spectral characterization of related substances of vardenafil, an erectile dysfunction drug
-
Vardenafil hydrochloride trihydrate (Levitra) is used to treat erectile dysfunction (ED) and is an inhibitor of phosphodiesterase type 5 (PDE-5) enzyme. It maintains higher levels of cyclic guanosine monophosphate (cGMP), relaxes smooth muscles, promotes penile blood flow, and enhances erectile function. During the bulk drug synthesis of vardenafil hydrochloride trihydrate, six related substances (impurities), vardenafil dimer, vardenafil N-oxide, vardenafil glycene, vardenafil oxopiperazine, vardenafil oxoacetic acid, and phenyl vardenafil were identified, and these are reported herein for the first time. The present work describes the synthesis and characterization of these impurities.
- Reddy, Vajrala Venkata,Naga Brahmeswara Rao, Mandava Venkata,Reddy, Ghanta Mahesh,Mukkanti, Khagga,Reddy, Ganta Madhusudhan
-
experimental part
p. 3513 - 3523
(2012/10/18)
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- Discovery and optimization of 2-phenyloxazole derivatives as diacylglycerol acyltransferase-1 inhibitors
-
In a discovery effort to find safe and effective DGAT-1 inhibitors, we have identified 2-phenyloxazole 4-carboxamide 1 as a conformationally constrained analog of a hydrazide hit, which was previously identified from high-throughput screening. Further optimization of this series has led to chemically more stable 2-phenyloxazole-based DGAT-1 inhibitor 25 with improved solubility, cell-based activity, and pharmacokinetic properties. Compound 25 also demonstrated in vivo efficacy in a diet-induced obesity (DIO) rat model.
- Yun, Weiya,Ahmad, Mushtaq,Chen, Yingsi,Gillespie, Paul,Conde-Knape, Karin,Kazmer, Sonja,Li, Shiming,Qian, Yimin,Taub, Rebecca,Wertheimer, Stanley J.,Whittard, Toni,Bolin, David
-
scheme or table
p. 7205 - 7209
(2012/01/15)
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- METHODS OF TREATING OR PREVENTING PSORIASIS, AND/OR ALZHEIMER'S DISEASE USING INDANE ACETIC ACID DERIVATIVES
-
The present invention provides indane acetic acid and their derivatives and methods for the treating and/or preventing psoriasis and/or Alzheimer's diseases.
- -
-
Page/Page column 141
(2010/12/29)
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- Synthesis and biological activity of a series of tetrasubstituted- imidazoles as P2X7 antagonists
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A series of analogues of the pyrazole lead 1 were synthesized in which the heterocyclic core was replaced with an imidazole. A number of potent antagonists were identified and structure-activity relationships (SAR) were investigated both with respect to activity at the P2X7 receptor and in vitro metabolic stability. Compound 10 was identified as a potent P2X7 antagonist with reduced in vitro metabolism and high solubility.
- Gleave, Robert J.,Walter, Daryl S.,Beswick, Paul J.,Fonfria, Elena,Michel, Anton D.,Roman, Shilina A.,Tang, Sac-Pham
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scheme or table
p. 4951 - 4954
(2010/10/04)
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- Brine-mediated efficient benzoylation of primary amines and amino acids
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Benzoylation of primary amines and amino acids is efficiently carried out in a brine solution using a stoichiometric amount of benzoyl chloride followed by trituration with aqueous saturated bicarbonate solution. Copyright Taylor & Francis Group, LLC.
- Chattopadhyay, Gautam,Chakraborty, Suchandra,Saha, Chandan
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experimental part
p. 4068 - 4075
(2009/04/11)
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- Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation
-
This invention relates to novel indane acetic acid derivatives which are useful in the treatment of diseases such as diabetes, obesity, hyperlipidemia, and atherosclerotic diseases. The invention also relates to intermediates useful in preparation of indane acetic derivatives and to methods of preparation.
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-
-
- Flow-vacuum pyrolysis of 2,5-diphenyl-4-methyloxazole
-
The flow-vacuum pyrolysis of 2,5-diphenyl-4-methyloxazole (4) at 1000°C and 0.5 Torr afforded a complex reaction mixture containing: benzonitrile, diphenylmethane, 9,10-dimethylphenantrene, 9,10-dimethylantracene, fluorene, o-benzylbenzonitrile (major product, 20-22%), phenanthrene, anthracene, o,o′-dicyanodiphenyl, 9,10-anthraquinone, 2-methyl-4,5-diphenyloxazole and 1,1,2,2-tetraphenylethane. A radical- and carbene mechanism is suggested in order to rationalize the formation of the reaction products.
- Banciu, Mircea D.,Istrati, Daniela,Schiketanz, Iosif,Mihǎiescu, Dan,Drǎghici, Constantin,Malacea, Raluca
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p. 493 - 499
(2007/10/03)
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- Highly enantioselective synthesis of α,β-diaminopropanoic acid derivatives using a catalytic asymmetric hydrogenation approach
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Rh-DuPhos-catalyzed asymmetric hydrogenation of α,β-diamidoacrylates provides a highly efficient and enantioselective route to chiral α,β-diaminopropanoic acid derivatives. The mechanistic course of the hydrogenation was studied using isotopically enriched enamide complexes and phosphorus and carbon NMR. Addition of methyl α-N-benzoyl-β-N-acetyl-diaminopropenoate to the solvated catalyst gave a single 1:1 enamide complex and demonstrated the binding of the olefin and α-amide carbonyl group; the carboxylate and β-N-acyl groups did not bind to the metal. Changes to the electronic and steric properties of the β-N-acyl group were well tolerated; however, small changes to the binding α-N-acyl group were found to significantly affect hydrogenation yields.
- Robinson,Chin Yu Lim,He,Ma,Li
-
p. 4141 - 4147
(2007/10/03)
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- Beauveria bassiana ATCC 7159 contains an L-specific α-amino acid benzamidase
-
Biotransformation of a series of racemic N-benzoyl α-amino acids by the fungus Beauveria bassiana ATCC 7159 results in isolation of the corresponding D-amino acid benzamides in high enantiomeric purity and yield.
- Holland, Herbert L.,Andreana, Peter R.,Salehzadeh-Asl, Reza,Van Vliet, Aaron,Ihasz, Nancy J.,Brown, Frances M.
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p. 667 - 672
(2007/10/03)
-
- Aminoketone, oxazole and thiazole synthesis. Part XIII. 1 new 2-aryl-6-phenyloxazoles with 4-methyl or 4-isopropyl groups
-
Benzoylation of (±)-α-alanine and (±)-valine followed by cyclization afforded the corresponding azlactones, which reacted with benzene, toluene, o- and m-xylene yielding substituted N-benzoyl-phenacylamines. Their cyclization in the presence of phosphorus oxychloride led to the title compounds whose electronic and NMR spectra (1H and 13C) are presented.
- Schiketanz, Iosif,Istrati, Daniela,Drǎghici, Constantin,Balaban, Alexandru T.
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p. 137 - 142
(2007/10/03)
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- Reactivity of the Amino Groups of α-Amino Acids and Dipeptides in Reaction with Benzoyl Chloride in a Dioxane-Water Solvent
-
The kinetic characteristics (rate constants, activation energies, and entropies of activation) for the reaction of a series of α-amino acids and dipeptides with benzoyl chloride in aqueous dioxane are presented.The amino group in the investigated α-amino acids has high reactivity 4 liter/mole*sec>; the dipeptides have lower reactivity 3 liter/mole*sec>.
- Kuritsyn, L. V.,Kalinina, N. V.
-
p. 767 - 770
(2007/10/02)
-
- Synthesis and in Vitro Aldolase Reductase Inhibitory Activity of Compounds Containing an N-Acylglycine Moiety
-
A number of N-benzoylglycines (6), N-acetyl-N-phenylglycines (7), N-benzoyl-N-phenylglycines (8), and tricyclic N-acetic acids (9-12) were synthesized as analogues of the N-acylglycine-containing aldolase reductase inhibitors alrestatin and 2-oxoquinoline-1-acetic acid.Derivatives of 6, which represent ring-simplified analogues of alrestatin, are very weak inhibitors of aldolase reductase obtained from rat lens, producing 50percent inhibition only at concentrations exceeding 100 μM.Compounds of series 7 were designed as ring-opened analogues of the 2-oxoquinolines.While this derivatives are more potent than compounds of series 6 (IC 50s of 6-80 μM), they are less active than the corresponding 2-oxoquinolines.Analogues of series 8 were designed as hybrid structures of both alrestatin and the 2-oxoquinoline-1-acetic acids.These compounds are substantially more potent than compounds of series 6 and 7 and display inhibitory activities comparable to or greater than alrestatin or the 2-oxoquinolines (IC 50s of 0.1-10 μM).Of the rigid analogues of 8, the most potent derivative is benzoxindol (12) with an IC 50 of 0.67 μM, suggesting that fusion of the two aromatic rings of 8 in a coplanar conformation may optimize affinity for aldose reductase in this series.
- DeRuiter, Jack,Swearingen, Blake E.,Wandrekar, Vinay,Mayfield, Charles A.
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p. 1033 - 1038
(2007/10/02)
-
- Composition containing a penem or carbapenem antibiotic and the use of the same
-
Administration of an N-acylated amino acid in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid derivative and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially.
- -
-
-
- DIISOPROPYLETHYLAMINE ELIMINATES DIPEPTIDE FORMATION DURING THE ACYLATION OF AMINO ACIDS USING BENZOYL CHLORIDE AND SOME ALKYL CHLOROFORMATES
-
Acylation of amino acids using benzoyl chloride in aqueous alkali leads to benzoylamino acids containing one percent of benzoyldipeptide.Use of diisopropylethylamine instead of sodium hydroxide as base eliminates the side reaction responsible for the contaminant.Ethoxycarbonylamino acids are advantageously prepared in the same manner using ethyl chloroformate or diethyl dicarbonate.The latter gives rise to some N-substituted dipeptide when used in aqueous alkali.The method is unsatisfactory for the benzyloxycarbonylation of amino acids.Use of 9-fluorenylmethyl chloroformate and diisopropylethylamine gives the pure derivative of leucine in moderate yield.
- Chen, Francis M. F.,Benoiton, N. Leo
-
p. 1224 - 1227
(2007/10/02)
-
- Composition containing a penem or carbapenem antibiotic
-
Administration of an N-acylated amino acid in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid derivative and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially. The composition may be prepared by simple mixing.
- -
-
-
- 1-Azadienes in Heterocyclic Synthesis. Reaction of 1-N-Alkyl-1-azapenta-1,3-dienes with Mesoionic Oxazolones
-
1-N-Alkyl-1-azapenta-1,3-dienes 2 smoothly reacted with various mesoionic oxazolones 1 to afford 3,4-dihydro-2-pyridones 3 in excellent yields and there is no evidence for the formation of any products arising from the cycloaddition on the carbon-carbon double bond or on the azomethine function.
- Sain, B.,Sandhu, J. S.
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p. 1007 - 1010
(2007/10/02)
-
- Studies on Potential Antibacterial and Chelating Agents: Part I - Synthesis, Physicochemical Properties and Antibacterial Screening of Some Benzimidazoles
-
Six properly substituted benzimidazoles (I-VI) suitable for chelation have been synthesised from benzoylamino acids by condensation with o-phenylenediamine following Phillips and fusion methods.Dissociation constants of the benzoyl derivatives of glycine, (dl)-α-alanine, β-alanine, L-(-)-aspartic acid, L-(+)-glutamic acid and the six protonated benzamidobenzimidazoles (I-VI) in water-dioxane (1:1) at constant ionic strength (μ=0.5) at 20 deg C +/- 0.1 deg C have been determined by potentiometric titration.Structures of I-VI have been established on the basis of their elemental analysis, synthetic route, IR and PMR spectra and pK* values.Some of the compounds show significant antibacterial activity against gram + ve organisms only whereas corresponding sulphonamidobenzimidazoles are active against the gram - ve organism E. coli.
- Nandi, M. M.,Ray, Ruma
-
p. 222 - 224
(2007/10/02)
-
- Kinetics of Racemization and Hydrolysis of Oxazol-5(4H)-ones
-
The kinetics of hydrolysis and ionization of three substrates, 4-benzyl-2-phenyl-, 4-methyl-2-phenyl- and 4-benzyl-2-methyl-oxazol-5(4H)-one have been investigated.Under neutral and basic conditions both reactions are buffer and hydroxide ion catalysed.In aqueous solution, ionization, leading to racemization of the optically active oxazolones, and ring opening occur competitively with similar rate constants.In solvents with lower dielectric constants, ionization becomes much faster than ring opening.An intermediate corresponding to a minor reaction pathway has been detected; it results probably from the addition of water to the C-N double bond.
- Daffe, Viviane,Fastrez, Jacques
-
p. 783 - 788
(2007/10/02)
-
- RELATIONSHIP BETWEEN STRUCTURE AND STEREOSPECIFICITY IN HYDROLYSIS OF OXAZOLONES CATALYZED WITH CYCLODEXTRINS
-
Four 5(4H)-oxazolones have been hydrolyzed in the presence of α- or β-cyclodextrin to yield corresponding acylamino acids.Kinetic studies, IR and UV spectra and product analyses have been used to analyze the complex pathways.The substrates and their conjugate anions form inclusion complexes.These complexes are then hydrolyzed either directly or through intermediate formation of an acyl-cyclodextrin.The reaction is enantioselective and there is a relationship between structure and stereoselectivity related to the fact that the mode of binding of the substrate appears to be largely controled by the presence of a phenyl in position 2.
- Daffe, Viviane,Fastrez, Jacques
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p. 327 - 333
(2007/10/02)
-
- Phenyl Selenide Anion, a Superior Reagent for the SN2 Cleavage of Esters and Lactones
-
The scope and limitations of SN2-type cleavages of esters and lactones with phenyl selenide anion are discussed.The reagent, when generated properly, is found to be an extremely potent nucleophile.However, its nucleophilicity can be greatly attenuated by varying the counterion and/or the degree of solvation of the anion.The reagent can be used in the presence of a variety of functional groups and exhibits a high degree of selectivity; e.g., methyl esters are selectively cleaved in the presence of ethyl esters.As the hindrance around the carbinol carbon increases, products derived from acyl oxygen cleavage are observed.The mechanistic implications of this are discussed.
- Liotta, Dennis,Sunay, Ustun,Santiesteban, Hector,Markiewicz, William
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p. 2605 - 2610
(2007/10/02)
-
