- A new enantioselective synthesis of β-amino acids
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Enantioselective hydrogenation of some α,β-unsaturated nitriles and their corresponding methyl esters bearing a phthalimidomethyl substituent at the α-carbon using Rh-DuPHOS catalysts afforded β-amino acid precursors with modest e.e.s of up to 48%. Hydrogenation of the α,β-unsaturated methyl esters using a Ru-BINAP catalyst gave higher e.e.s of up to 84%. Method development for the determination of the enantiomeric excesses of these derivatives using chiral HPLC is also reported.
- Saylik, Dilek,Campi, Eva M.,Donohue, Andrew C.,Jackson,Robinson, Andrea J.
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- Diastereoselective total synthesis and structural confirmation of surugamide F
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Surugamide F is a linear decapeptide (1) isolated along with the cyclic octapeptides surugamides A–E (2–6), from a marine-derived Streptomyces species. The linear peptide 1 is produced by two nonribosomal peptide synthetases (NRPSs) encoded in adjacent open reading frames, which are further flanked by an additional pair of NRPS genes responsible for the biosyntheses of the cyclic peptides 2–6. While the cyclic peptides 2–6 were identified to be cathepsin B inhibitors, the biological activity of the new metabolite 1 still remained unclear. In order to elucidate its unique biosynthetic pathway and biological activity in detail, we planned to develop an efficient synthetic route toward 1. Here we report the diastereoselective total synthesis of 1, utilizing 9-fluorenylmethyloxycarbonyl (Fmoc)-based solid-phase peptide synthesis. During this study, we found that the structural correction of 1 was required, due to the mislabeling of the commercially obtained 3-amino-2-methylpropionic acid, and the true structure of 1 was corroborated by the chemical synthesis and chromatographic comparison.
- Kuranaga, Takefumi,Fukuba, Atsuki,Ninomiya, Akihiro,Takada, Kentaro,Matsunaga, Shigeki,Wakimoto, Toshiyuki
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- Meteorites as catalysts for prebiotic chemistry
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From outer space: Twelve meteorite specimens, representative of their major classes, catalyse the synthesis of nucleobases, carboxylic acids, aminoacids and low-molecular-weight compounds from formamide (see figure). Different chemical pathways are identified, the yields are high for a prebiotic process and the products come in rich and composite panels.
- Saladino, Raffaele,Botta, Giorgia,Delfino, Michela,Di Mauro, Ernesto
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- New biocatalytic route for the production of enantioenriched β-alanine derivatives starting from 5- and 6-monosubstituted dihydrouracils
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Taking advantage of the catalytic promiscuity of pyrimidine-catabolism enzymes (dihydropyrimidinase (E.C. 3.5.2.2), N-carbamoyl-β-alanine amidohydrolase (E.C. 3.5.1.6)), the production of different β-alanine derivatives starting from 5- and 6-monosubstituted dihydrouracils has been evaluated using a mimesis approach. In this work, the S-enantioselective character of dihydropyrimidinase from Sinorizhobium meliloti toward 6-monosubstituted dihydrouracil derivatives has been shown. An inverted R-/S-enantioselectivity of N-carbamoyl-β-alanine amidohydrolase from Agrobacterium tumefaciens toward two different N-carbamoyl-β-amino acids has been proved. Our results have shown for the first time that this mimetic tandem constitutes an interesting biotechnological tool for the preparation of different β-alanine derivatives in an environmentally friendly way, allowing the production of enantioenriched (R)-α-phenyl-β-alanine (e.e. > 95%) and (R)-α-methyl-β-alanine (e.e. > 90%).
- Martínez-Gómez, Ana Isabel,Clemente-Jiménez, Josefa María,Rodríguez-Vico, Felipe,Kanerva, Liisa T.,Li, Xiang-Guo,Heras-Vázquez, Francisco Javier Las,Martínez-Rodríguez, Sergio
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- Absolute Configuration and Antibiotic Activity of Piceamycin
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The cultivation of a Streptomyces sp. SD53 strain isolated from the gut of the silkworm Bombyx mori produced two macrolactam natural products, piceamycin (1) and bombyxamycin C (2). The planar structures of 1 and 2 were identified by a combination of NMR, MS, and UV spectroscopic analyses. The absolute configurations were assigned based on chemical and chromatographic methods as well as ECD calculations. A new chromatography-based experimental method for determining the configurations of stereogenic centers β to nitrogen atoms in macrolactams was established and successfully applied in this report. These compounds exhibited significant bioactivities against the silkworm entomopathogen Bacillus thuringiensis and various human pathogens as well as human cancer cell lines. In particular, piceamycin potently inhibited Salmonella enterica and Proteus hauseri with MIC values of 0.083 μg/mL and 0.025 μg/mL, respectively. The biosynthetic pathway involved in the formation of the cyclopentenone moiety in piceamycin is discussed.
- Beom, Ji Yoon,Byun, Woong Sub,Chung, Beomkoo,Hong, Suckchang,Jeon, Chang-Wook,Kang, Saeyeon,Kwak, Youn-Sig,Lee, Jeeyeon,Lee, Sang Kook,Oh, Dong-Chan,Oh, Ki-Bong,Shin, Jongheon,Shin, Yern-Hyerk,Yoon, Yeo Joon
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- Modular Enzymatic Cascade Synthesis of Vitamin B5 and Its Derivatives
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Access to vitamin B5 [(R)-pantothenic acid] and both diastereoisomers of α-methyl-substituted vitamin B5 [(R)- and (S)-3-((R)-2,4-dihydroxy-3,3-dimethylbutanamido)-2-methylpropanoic acid] was achieved using a modular three-step biocatalytic cascade involving 3-methylaspartate ammonia lyase (MAL), aspartate-α-decarboxylase (ADC), β-methylaspartate-α-decarboxylase (CrpG) or glutamate decarboxylase (GAD), and pantothenate synthetase (PS) enzymes. Starting from simple non-chiral dicarboxylic acids (either fumaric acid or mesaconic acid), vitamin B5 and both diastereoisomers of α-methyl-substituted vitamin B5, which are valuable precursors for promising antimicrobials against Plasmodium falciparum and multidrug-resistant Staphylococcus aureus, can be generated in good yields (up to 70 %) and excellent enantiopurity (>99 % ee). This newly developed cascade process may be tailored and used for the biocatalytic production of various vitamin B5 derivatives by modifying the pantoyl or β-alanine moiety.
- Abidin, Mohammad Z.,Saravanan, Thangavelu,Zhang, Jielin,Tepper, Pieter G.,Strauss, Erick,Poelarends, Gerrit J.
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- Stereochemistry of the Metabolism of the DNA Base Thymine and the Drug 5-Fluorouracil
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The enzyme dihydrothymine dehydrogenase reduces both the DNA base thymine and the anti-cancer drug 5-fluorouracil by overall trans addition of hydrogen, at the si-face at C-5 and the si-face at C-6.
- Gani, David,Hitchcock, Peter B.,Young, Douglas W.
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- Tripartilactam, a cyclobutane-bearing tricyclic lactam from a Streptomyces sp. in a dung beetle's brood ball
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Tripartilactam, a structurally unprecedented cyclobutane-bearing tricyclic lactam metabolite, was discovered from Streptomyces sp. isolated from a brood ball of the dung beetle, Copris tripartitus. The structure of this compound was elucidated by the combination of NMR, MS, UV, and IR spectroscopy and multistep chemical derivatization. Tripartilactam was evaluated as a Na+/K + ATPase inhibitor (IC50 = 16.6 μg/mL).
- Park, Seon-Hui,Moon, Kyuho,Bang, Hea-Son,Kim, Seong-Hwan,Kim, Dong-Gyu,Oh, Ki-Bong,Shin, Jongheon,Oh, Dong-Chan
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- Stereoselective α-alkylation of new chiral auxiliaries: An access to enantiomerically pure α- and α,β-substituted β-amino acids
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New bicyclic heterocycles 5, which are potentially useful for the enantioselective synthesis of substituted β-amino acids, have been synthesized. A study on the α-alkylation of these chiral auxiliaries is presented. An optically pure β-amino acid was obtained in excellent yield from its masked chiral derivative 6a.
- Agami, Claude,Cheramy, Sandrine,Dechoux, Luc
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- The Formation of Amino Acids by the Reactions of Singlet NH with Several Carboxylic Acids
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The photolysis of hydrogen azide was studied in liquid acetic acid, propionic acid, and isobutyric acid at room temperature.The formation of amino acids was confirmed by the color reactions with ninhydrin and with chromotropic acid and by the NMR spectra.From the propionic acid, α- and β-alanine were formed in the ratio of 1.5.In the case of isobutyric acid, α- and β-aminoisobutyric acids were formed in the ratio of about 5.These results are explained by the insertion reaction of NH(a1Δ) into the C-H bonds of carboxylic acids.
- Tsunashima, Shigeru,Kitamura, Takashi,Sato, Shin
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- Catalytic Asymmetric Synthesis of Unprotected β2-Amino Acids
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We report here a scalable, catalytic one-pot approach to enantiopure and unmodified β2-amino acids. A newly developed confined imidodiphosphorimidate (IDPi) catalyzes a broadly applicable reaction of diverse bis-silyl ketene acetals with a silylated aminomethyl ether, followed by hydrolytic workup, to give free β2-amino acids in high yields, purity, and enantioselectivity. Importantly, both aromatic and aliphatic β2-amino acids can be obtained using this method. Mechanistic studies are consistent with the aminomethylation to proceed via silylium-based asymmetric counteranion-directed catalysis (Si-ACDC) and a transition state to explain the enantioselectivity is suggested on the basis of density functional theory calculation.
- Zhu, Chendan,Mandrelli, Francesca,Zhou, Hui,Maji, Rajat,List, Benjamin
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supporting information
p. 3312 - 3317
(2021/04/07)
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- METHODS AND MATERIALS FOR ASSESSING AND TREATING OBESITY
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This document relates to methods and materials for assessing and/or treating obese mammals (e.g., obese humans). For example, methods and materials for using one or more interventions (e.g., one or more pharmacological interventions) to treat obesity and/or obesity-related comorbidities in a mammal (e.g., a human) identified as being likely to respond to a particular intervention (e.g., a pharmacological intervention) are provided.
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- β2-Homo-amino acid scan of μ-selective opioid tetrapeptide TAPP
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TAPP (H-Tyr-d-Ala-Phe-Phe-NH2) is a potent, μ-selective opioid ligand. In order to gain further insights into pharmacophoric features of this tetrapeptide, we have performed a β2-Homo-amino acid (β2hAA) scan of the TAPP sequence. To this aim, 10 novel analogues have been synthesized and evaluated for μ-opioid and δ-opioid receptor affinity as well as for stability in human plasma. The derivatives included compounds in which a (R)- or (S)-β2-Homo-Homologue replaced the amino acids in the TAPP sequence. The derivatives with (R)- or (S)-β2hPhe4 turned out to bind μOR with affinities equal to that of the parent. β2hAAs in position 1 and 3 resulted in rather large affinity decreases, but the change differed depending on the stereochemistry. β2-Homologation in the second position gave derivatives with very poor μOR binding. According to molecular modelling, the presented α/β-peptides adopt a variety of binding poses with their common element being an ionic interaction between a protonable amine of the first residue and Asp147. A feature required for high μOR affinity seems the ability to accommodate the ring in the fourth residue in a manner similar to that found for TAPP. Contrary to what might be expected, several compounds were significantly less stable in human plasma than the parent compound.
- Kosson, Piotr,Lipiński, Piotr F. J.,Misicka, Aleksandra,Tymecka, Dagmara
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- Bombyxamycins A and B, Cytotoxic Macrocyclic Lactams from an Intestinal Bacterium of the Silkworm Bombyx mori
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Bombyxamycins A and B (1 and 2) were discovered from a silkworm gut Streptomyces bacterium. Spectroscopic analysis and multiple-step chemical derivatization identified them as 26-membered cyclic lactams with polyene features. Bombyxamycin A showed significant antibacterial and antiproliferative effects. The bombyxamycin biosynthetic gene cluster was identified by genetic analysis. Gene deletion experiments confirmed that the cytochrome P450 BomK is responsible for the generation of 2, which unprecedentedly bears tetrahydrofuran in its macrocyclic ring.
- Shin, Yern-Hyerk,Beom, Ji Yoon,Chung, Beomkoo,Shin, Yoonho,Byun, Woong Sub,Moon, Kyuho,Bae, Munhyung,Lee, Sang Kook,Oh, Ki-Bong,Shin, Jongheon,Yoon, Yeo Joon,Oh, Dong-Chan
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supporting information
p. 1804 - 1808
(2019/03/11)
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- Asymmetric synthesis of β2-amino acids: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives
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Conjugate addition of lithium dibenzylamide to (S)-N(3)-acryloyl-4- isopropyl-5,5-dimethyloxazolidin-2-one (derived from l-valine) and alkylation of the resultant lithium β-amino enolate provides, after deprotection, a range of (S)-2-alkyl-3-aminopropanoic acids in good yield and high ee. Alternatively, via a complementary pathway, conjugate addition of a range of secondary lithium amides to (S)-N(3)-(2′-alkylacryloyl)-4-isopropyl-5,5- dimethyloxazolidin-2-ones, diastereoselective protonation with 2-pyridone, and subsequent deprotection furnishes a range of (R)-2-alkyl- and (R)-2-aryl-3-aminopropanoic acids in good yield and high ee. Additionally, the boron-mediated aldol reaction of β-amino N-acyl oxazolidinones is a highly diastereoselective method for the synthesis of a range of β-amino- β′-hydroxy N-acyl oxazolidinones. The Royal Society of Chemistry.
- Beddow, James E.,Davies, Stephen G.,Ling, Kenneth B.,Roberts, Paul M.,Russell, Angela J.,Smith, Andrew D.,Thomson, James E.
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p. 2812 - 2825
(2008/03/12)
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- One-pot synthesis of β-amino acid derivatives via addition of bis(O-silyl) ketene acetals on iminium salts
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We report here our findings on a new and highly efficient strategy for the synthesis of β-amino acids involving the addition of bis(O-silyl) ketene acetals on Mannich type iminium electrophiles.
- Moumné, Roba,Denise, Bernard,Parlier, Andrée,Lavielle, Solange,Rudler, Henri,Karoyan, Philippe
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p. 8277 - 8280
(2008/03/30)
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- Efficient synthesis of β2-amino acid by homologation of α-amino acids involving the reformatsky reaction and Mannich-type imminium electrophile
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Development of new methods for the synthesis of β-amino acids is important as polymers of these compounds are promising peptidomimetic candidates in medicinal chemistry. We report here our findings on a new and highly efficient general strategy for the synthesis of β2-amino acids by homologation of α-amino acids, involving the Reformatsky reaction and Mannich-type imminium electrophile.
- Moumne, Roba,Lavielle, Solange,Karoyan, Philippe
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p. 3332 - 3334
(2007/10/03)
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- Asymmetric synthesis of substituted azetidine type α- and β-amino acids
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A versatile asymmetric synthesis of 3-substituted azetidine-2-carboxylic acids and 2-substituted azetidine-3-carboxylic acids via 1,3-amino alcohols with excellent stereoselectivities (de ≥ 96%, ee ≥ 96%) is reported. The high asymmetric inductions were achieved employing the SAMP/RAMP-hydrazone methodology. A phenyl moiety was used as a synthetic equivalent of the carboxylic acid function. In addition, the amino acids prepared were tested as organocatalysts in an asymmetric aldol reaction. Georg Thieme Verlag Stuttgart.
- Enders, Dieter,Gries, Joerg
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p. 3508 - 3516
(2007/10/03)
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- Enantioselective synthesis of β-amino acids Part 13. Diastereoselective alkylation of dianions derived from chiral analogs of β-aminopropanoic acid containing the α-phenylethyl group
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Inexpensive acryloyl chloride was converted in 91% overall yield to two derivatives of β-alanine, (R,R,R)-and (R,R,S)-6, containing two chiral auxiliaries. C-Alkylation of (R,R,R)- and (R,R,S)-6 via a dianion derivative, was performed by direct metallation with 2.2 equiv. of lithium hexamethyldisilazane (LHMDS) in THF at - 78°. C-Alkylation of (R,R,S)-6-Li2 ('matched' pair of chiral auxiliaries) afforded the mono-alkylated products 8-11 in 29-96% yield and 54-95% stereoselectivity. Employment of LiCl as an additive generally increased stereoselectivities, whereas the effect of HMPA as a cosolvent was erratic. Chemical correlation of the major diastereoisomer from the alkylation reactions with (S)-α-alkyl-β-alanine (12-15) showed that addition of the electrophile preferentially takes place on the enolate's Si-face. This conclusion is also supported by molecular-modeling studies (ab initio HF/3-21G), which indicate that the lowest-energy conformation for (R,R,S)-6-Li2 presents the more sterically hindered Re-face of the enolate. The theoretical studies also predict a determining role for N-Li-O chelation in (R,R,S)-6-Li2, giving rise to an interesting 'ion-triplet' configuration for the dilithium dianion.
- Gutierrez-Garcia, Victor Manuel,Reyes-Rangel, Gloria,Munoz-Muniz, Omar,Juaristi, Eusebio
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p. 4189 - 4199
(2007/10/03)
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- Enantioselective synthesis of α,β-substituted β-amino acids
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Chiral derivative 3 was shown to be a precursor of α and β-substituted β-amino acids as well as α,β-disubstituted β-amino acids. The key steps of the procedure are a diastereoselective alkylation of synthon 3 by organocuprates reagents and a diastereoselective alkylation of the alkylated adduct.
- Agami, Claude,Cheramy, Sandrine,Dechoux, Luc,Melaimi, Mohand
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p. 195 - 200
(2007/10/03)
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- Synthesis of alpha-substituted beta-amino acids using pseudoephedrine as a chiral auxiliary.
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[reaction: see text] beta-Amino acids are becoming increasingly attractive as intermediates in the synthesis of a variety of molecular structures. However, few methods are available for the synthesis of alpha-substituted beta-amino acids that are both readily scalable and highly stereoselective. Herein we report a new method for synthesizing alpha-substituted beta-amino acids that satisfies both of these requirements using enantiomerically pure pseudoephedrine as a chiral auxiliary.
- Nagula,Huber,Lum,Goodman
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p. 3527 - 3529
(2007/10/03)
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- Palladium-catalysed asymmetric allylic substitution: Synthesis of α- and β-amino acids
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Methodology has been established for the formation of enantiomerically enriched α-amino acids using palladium-catalysed allylic amination. The formation of enantiomerically enriched allylamines has been achieved with high enantioselectivity. Oxidative cleavage of the allylamines provides arylglycine and glutamic acid derivatives. Additionally, enantiomerically enriched β-amino acids have been prepared in high enantiomeric excess. Palladium-catalysed asymmetric allylic substitution is used as the key synthetic transformation.
- Bower, Justin F.,Jumnah, Roshan,Williams, Andrew C.,Williams, Jonathan M. J.
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p. 1411 - 1420
(2007/10/03)
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- Peptides with an insulin-like action
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Peptides with an insulin-like action, of formula I: STR1 in which G is a hydrogen atom, an amino add residue, or a monosubstituted or polysubstituted amino acid; D is an amino acid residue, a phosphoamino acid residue, a monosaccharide residue, or a covalent bond; E is --NH--(CH2)n --NR52, a glycerol residue, or --NH--(CH2)p --R6 --R7 ; R1 is (C1 -C4)-alkyl or =O; R2 is a sulfhydryl protecting group, (C1 -C3)-alkyl, or a hydrogen atom; R3 and R4, independently of one another, are a hydrogen atom or methyl; R5, each being identical or different, is a hydrogen atom, 1 to 6 monosaccharide residues, or 1 to 6 monosubstituted or polysubstituted monosaccharide residues; R6 is O PO4 H, PO2 H, NHCOO, S or OCOO; R7 is a hydrogen atom, 1 to 6 monosaccharide residues, or 1 to 6 monosubstituted or polysubstituted monosaccharide residues; w is an integer 1 or 2; their preparation and use for treatment of diabetes mellitus or insulin-independent diabetes.
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- Enantioselective synthesis of β-amino acids. 7. Preparation of enantiopure α-substituted β-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one
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Inexpensive natural α-amino acid L-asparagine was efficiently converted to either (R)- or (S)-α-alkylated β-amino acids in enantiomerically pure state. The key intermediate in this protocol is the enantiopure N,N-acetal pyrimidinone (S)-1, a masked chiral derivative of β-alanine.
- Juaristi, Eusebio,Quintana, Delia,Balderas, Margarita,Garcia-Perez, Enrique
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p. 2233 - 2246
(2007/10/03)
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- 3-Methylazetidin-2-one and its precursors: Optical resolution and absolute configurations
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Enantiomers of 3-methylazetidin-2-one - (3R)-(+)- and (3S)-(-)-1 and 3-amino-2-methylpropionic acid - (2R)-(-)- and (2S)-(+)-2 were obtained from corresponding diastereomers of methyl (αS)-N-α-methylbenzyl-3-amino-2-methylpropionate 3A,B which had been separated by recrystallization of their salts 4A,B with p-toluenesulfonic acid. The absolute configurations of azetidinones (+)- and (-)-1 and their diastereomeric precursors, i.e. amino esters 3A,B, (αS)-N-α-methylbenzyl-3-amino-2-methylpropionic acids 5A,B, and (αS)-N-α-methylbenzyl-3-methylazetidin-2-ones 6A,B were established by conversion of (+)-1 to amino acid (2R)-(-)-2 and of amino acid (2S)-(+)-2 to (-)-1.
- Shustov,Rauk
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p. 699 - 708
(2007/10/03)
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- Asymmetric Synthesis of β-Amino Acids. 1. Highly Diastereoselctive Addition of a Racemic β-Alanine Enolate Derivative to Electrophiles
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β-Alanine, an inexpensive β-amino acid, was converted into the 2-tert-butylperhydropyrimidin-4-one derivative 2, which can be alkylated with high stereoselectivity via the corresponding enolate.The high diastereoselectivity observed for the reaction of 2-Li with electrophiles seems to be due to steric hindrance generated by an axial disposition of the tert-butyl group at C(2), which directs addition from the enolate face opposite to this group.The hydrolysis of the resulting adducts proceeds with 6N hydrochloric acid to affford α-substituted β-amino acids in good yields.These results pave the road to the development of a new asymmetric synthesis of enantiomerically pure α-substituted β-amino acids.
- Juaristi, Eusebio,Quintana, Delia,Lamatsch, Bernd,Seebach, Dieter
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p. 2553 - 2557
(2007/10/02)
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- FLAME-INDUCED CARBOXYLATION OF UNSATURATED AMINES IN AN AQUEOUS FORMIC ACID SOLUTION
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When a hydrogen-oxygen flame was kept in contact with an aqueous formic acid solution of unsaturated amines, carboxylation onto a double bond took place.This reaction revealed to be initiated by addition of a hydrogen atom to the double bond followed by coupling of the resulted substrate radical with a carboxyl radical.
- Nomoto, Shinya,Harada, Kaoru
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p. 145 - 148
(2007/10/02)
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- Stereochemistry of Catabolism of the DNA Base Thymine and of the Anticancer Drug 5-Fluorouracil
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(2S)-3-Amino-2-methylpropanoic acid (6) and (2RS,3S)--3-amino-2-methylpropanoic acid (14) have been synthesized and used to provide an assay which shows that the catabolism of the DNA base thymine (1; R = Me) proceeds by overall anti addition of hydrogen to the pyrimidine at the si face at C-5 and the si face at C-6.X-Ray structure analysis of a derivative of the product of reaction of N,N-dibenzyl-L-serine methyl ester (15; R = Me) with (diethylamino)sulphur trifluoride followed by deprotection has shown it to be (2R)-3-amino-2-fluoropropanoic acid (19; R = H).This was identical with the product of catabolism of the anti-cancer drug 5-fluorouracil (1; R = F).Esters of (2R,3S)-- and (2R,3R)--3-amino-2-fluoropropanoic acids have been synthesized and used to provide an assay which shows that catabolism of the anti-cancer drug 5-fluorouracil (1; R = F) proceeds with the same absolute stereochemistry as is found in catabolism of thymine (1; R = Me).
- Gani, David,Hitchcock, Peter B.,Young, Douglas W.
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p. 1363 - 1372
(2007/10/02)
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- ORIENTATION OF CARBOXYLATION REACTION BY CONTACT GLOW DISCHARGE ELECTROLYSIS
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The carboxylation reaction of aliphatic amines and cyclic imines in aqueous formic acid by contact glow discharge electrolysis (CDGE) was studied and the orientation of the carboxylation reaction was investigated.It was found that orientation of the reaction was controlled by the effect of the charged and uncharged nitrogen atom.
- Terasawa, Jun-ichi,Harada, Kaoru
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