- A π–Cu(II)?π Complex as an Extremely Active Catalyst for Enantioselective α-Halogenation of N-Acyl-3,5-dimethylpyrazoles
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Novel chiral π–copper(II)?π complex catalyzed enantioselective α-chlorination and -bromination of N-acyl-3,5-dimethylpyrazoles are described. The π–copper(II)?π complexation of Cu(OTf)2 with 3-(2-naphthyl)-l-alanine-derived amides greatly increases the Lewis acidity and triggers the in situ generation of enolate species without an external base, which has a suppressing effect for α-chlorination and -bromination due to undesired halogen bonding. This strategy provides facile access to α-halogenated compounds in high yield with excellent enantioselectivity. X-ray crystallographic and ESR analyses of the catalyst complexes suggest that the release of two counteranions (2TfO–) from the copper(II) center might be crucial for the efficient activation of N-acyl-3,5-dimethylpyrazoles.
- Nishimura, Kazuki,Wang, Yanzhao,Ogura, Yoshihiro,Kumagai, Jun,Ishihara, Kazuaki
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p. 1012 - 1017
(2022/01/19)
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- Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions
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The asymmetric α-chlorination of activated aryl acetic acid esters can be carried out with high levels of enantioselectivities utilizing commercially available isothiourea catalysts under base-free conditions. The reaction, which proceeds via the in situ formation of chiral C1 ammonium enolates, is best carried out under cryogenic conditions combined with a direct trapping of the activated α-chlorinated ester derivative to prevent epimerization, thus allowing for enantioselectivities of up to e.r. 99:1.
- Stockhammer, Lotte,Weinzierl, David,B?gl, Thomas,Waser, Mario
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p. 6143 - 6147
(2021/08/18)
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- Visible Light-Promoted Sulfoxonium Ylides Synthesis from Aryl Diazoacetates and Sulfoxides
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A visible light-promoted reaction of donor/acceptor diazoalkanes with sulfoxides towards the synthesis of synthetically useful sulfoxonium ylides was reported. The reaction occurred under sole visible light irradiation without the need of any transition-metals or additives, affording the corresponding sulfoxonium ylides in moderate to good yields. The success of late-stage modification of natural isolates or drug candidates, scale-up reaction and transformation of sulfoxonium ylides to other useful molecules further rendered the approach valuable.
- Lu, Juan,Li, Lei,He, Xiang-Kui,Xu, Guo-Yong,Xuan, Jun
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p. 1646 - 1650
(2021/05/28)
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- [3 + 2] Cycloaddition of α-Aryl-α-diazoacetates with Terminal Alkynes via the Cooperative Catalysis of Palladium and Acid
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Palladium and acid cooperative catalysis is presented as a strategy for the [3 + 2] cycloaddition of acceptor/donor-type diazo compounds with terminal alkynes. The [3 + 2] cycloaddition of α-aryl-α-diazoacetates with terminal alkynes proceeded smoothly to produce 2,3,5-trisubstituted furans with high yields. This synthesis method provided a direct and efficient pathway to prepare furan ring-containing organosilane and organoboron reagents. Synthetically valuable functional groups such as chloro and bromo atoms, methoxycarbonyl, and carbonyl remained intact during the [3 + 2] cycloaddition reaction.
- Guo, Hongyu,Zhang, Sheng,Yu, Xiaoqiang,Feng, Xiujuan,Yamamoto, Yoshinori,Bao, Ming
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p. 10789 - 10795
(2021/09/08)
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- Straightforward Access to Terminally Disubstituted Electron-Deficient Alkylidene Cyclopent-2-en-4-ones through Olefination with α-Carbonyl and α-Cyano Secondary Alkyl Sulfones
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Herein we report on a simplified synthesis of scarcely explored, terminally disubstituted electron-poor alkylidene cyclopent-2-en-4-ones through uncommon olefination. Secondary sulfones, activated by electron-withdrawing groups at the adjacent carbon atom, undergo K2CO3-promoted coupling with 4-acyloxy- and 4-tert-butyldimethylsilyloxycyclopent-2-en-1-ones giving directly, or after a separate dehydrosulfinylation step, alkylidene cyclopent-2-en-4-ones. A plausible mechanism for these transformations is proposed. Initially, β-arylsulfonyl esters as well as their acetyl or nitrile analogues are allylated by cyclopentenone derivatives via a tandem Michael addition of α-sulfonyl carbanions followed by proton migration and retro-Michael-type O-nucleofuge elimination. The primary allylation products are formed as two diastereomers whose configuration and conformation were elucidated using single crystal X-ray diffraction and NMR spectroscopy. Regardless of stereochemistry, both sets of diastereomers are subjected to Zaitsev-type retro-Michael vinylogous dehydrosulfinylation under either basic or thermal silica gel promoted conditions resulting in E/Z-alkylidene cyclopent-2-en-4-ones. In these reactions activated sulfones serve as bearing electron-withdrawing group alkylidene anion-radical synthons, whereas 4-oxy-substituted cyclopentenones represent cyclopent-2-en-4-one cation-radical surrogates.
- Afri, Michal,Gruzman, Arie,Korshin, Edward E.,Leitus, Gregory,Palczewski, Krzysztof,Rothstein, Ayelet,Trifonov, Lena,Viskind, Olga
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supporting information
p. 6725 - 6736
(2021/12/31)
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- Lewis Base Catalysis Enables the Activation of Alcohols by means of Chloroformates as Phosgene Substitutes
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Nucleophilic substitutions (SN) are typically promoted by acid chlorides as sacrificial reagents to improve the thermodynamic driving force and lower kinetic barriers. However, the cheapest acid chloride phosgene (COCl2) is a highly toxic gas. Against this background, phenyl chloroformate (PCF) was discovered as inherently safer phosgene substitute for the SN-type formation of C?Cl and C?Br bonds using alcohols. Thereby, application of the Lewis bases 1-formylpyrroldine (FPyr) and diethylcyclopropenone (DEC) as catalysts turned out to be pivotal to shift the chemoselectivity in favor of halo alkane generation. Primary, secondary and tertiary, benzylic, allylic and aliphatic alcohols are appropriate starting materials. A variety of functional groups are tolerated, which includes even acid labile moieties such as tert-butyl esters and acetals. Since the by-product phenol can be isolated, a recycling to PCF with inexpensive phosgene would be feasible on a technical scale. Eventually, a thorough competitive study demonstrated that PCF is indeed superior to phosgene and other substitutes.
- Zoller, Ben,Stach, Tanja,Huy, Peter H.
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p. 5637 - 5643
(2020/09/21)
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- A Phosphorus(III)-Mediated (4+1)-Cycloaddition of 1,2-Dicarbonyls and Aza-o-Quinone Methides to Access 2,3-Dihydroindoles
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A (4+1)-cycloaddition is reported between 1,2-dicarbonyls and aza-o-quinone methide precursors to access 2,3-dihydroindoles bearing a tetra-substituted carbon center. The utilization of dioxyphospholenes as carbene surrogates provided dihydroindoles in 20–90 % yield, wherein the electronic nature of the dioxyphospholene impacts its role in the reaction.
- Eckert, Kaitlyn E.,Lepore, Antonio J.,Ashfeld, Brandon L.
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- A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions
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A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.
- Huy, Peter H.,Filbrich, Isabel
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supporting information
p. 7410 - 7416
(2018/04/30)
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- Systematic Evaluation of Sulfoxides as Catalysts in Nucleophilic Substitutions of Alcohols
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Herein, a method for the nucleophilic substitution (SN) of benzyl alcohols yielding chloro alkanes is introduced that relies on aromatic sulfoxides as Lewis base catalysts (down to 1.5 mol-%) and benzoyl chloride (BzCl) as reagent. A systematic screening of various sulfoxides and other sulfinyl containing Lewis bases afforded (2-methoxyphenyl)methyl sulfoxide as optimal catalyst. In contrast to reported formamide catalysts, sulfoxides also enable the application of plain acetyl chloride (AcCl) as reagent. In addition, it was demonstrated that weakly electrophilic carboxylic acid chlorides like BzCl promote Pummerer rearrangement of sulfoxides already at room temperature. This side-reaction also provided the explanation, why sulfoxide catalyzed SN-reactions of alcohols do not allow the effective production of aliphatic and electron deficient chloro alkanes. Comparison experiments provided further insight into the reaction mechanism.
- Motsch, Sebastian,Schütz, Christian,Huy, Peter H.
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supporting information
p. 4541 - 4547
(2018/09/13)
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- A mild method for the replacement of a hydroxyl group by halogen. 1. Scope and chemoselectivity
-
α-Chloro-, bromo- and iodoenamines, which are readily prepared from the corresponding isobutyramides have been found to be excellent reagents for the transformation of a wide variety of alcohols or carboxylic acids into the corresponding halides. Yields are high and conditions are very mild thus allowing for the presence of sensitive functional groups. The reagents can be easily tuned allowing therefore the selective monohalogenation of polyhydroxylated molecules. The scope and chemoselectivity of the reactions have been studied and reaction mechanisms have been proposed.
- Munyemana, Fran?ois,George, Isabelle,Devos, Alain,Colens, Alain,Badarau, Eduard,Frisque-Hesbain, Anne-Marie,Loudet, Aurore,Differding, Edmond,Damien, Jean-Marie,Rémion, Jeanine,Van Uytbergen, Jacqueline,Ghosez, Léon
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p. 420 - 430
(2015/12/31)
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- METHOD OF CONVERTING ALCOHOL TO HALIDE
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The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.
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Page/Page column 51; 127; 131
(2017/01/02)
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- CaF2 catalyzed SN2 type chlorodehydroxylation of chiral secondary alcohols with thionyl chloride: A practical and convenient approach for the preparation of optically active chloroalkanes
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A CaF2 catalyzed chlorodehydroxylation of chiral secondary alcohols with thionyl chloride has been developed. The chlorination reaction is effective for a wide range of alcohols, generating the corresponding chloroalkanes in good yield with high optical purity with inversion of the original configuration of the alcohol.
- Zhang, Junjie,Wang, Huanxia,Ma, Yun,Wang, Youming,Zhou, Zhenghong,Tang, Chuchi
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p. 2261 - 2263
(2013/05/09)
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- Dihaloiodoarenes: α,α-dihalogenation of phenylacetate derivatives
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A hypervalent iodine reagent-based α-carbonyl dihalogenation reaction is reported. Treating diazoacetate derivatives with either iodobenzene dichloride or iodotoluene difluoride results in gem-dichlorination or gem-difluorination products, respectively. The reaction is catalyzed by either Lewis acid or Lewis base activation of the aryl-λ3-iodane (ArIX2) species and proceeds rapidly and chemoselectively to the desired gem-difunctionalized products in good to excellent yield.
- Tao, Jason,Tran, Richard,Murphy, Graham K.
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p. 16312 - 16315
(2013/12/04)
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- Copper-catalyzed amination of silyl ketene acetals with N-chloroamines
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A copper(I)/2,2′-bipyridyl complex catalyzes an amination reaction of silyl ketene acetals with N-chloroamines, presenting a new preparative method of α-amino esters.
- Miura, Tomoya,Morimoto, Masao,Murakami, Masahiro
-
supporting information
p. 5214 - 5217,4
(2020/09/02)
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- 1,2-Dimethoxy-4,5-dimethylene: A new protecting group for acyclic amino acid derivatives prepared by Stevens rearrangement
-
A new protecting group, 1,2-dimethoxy-4,5-dimethylene, for acyclic amino acid derivatives could be introduced by N,N-dialkylation with 1,2-bis(bromomethyl)-4,5-dimethoxybenzene (1) and removed via amine de-alkylation with acyl chlorides. The method can be used with base-induced [2,3] and [1,2] Stevens rearrangement products.
- Tayama, Eiji,Takedachi, Keisuke,Iwamoto, Hajime,Hasegawa, Eietsu
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supporting information; experimental part
p. 1373 - 1375
(2012/03/27)
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- A formal method for the de-N,N-dialkylation of Sommelet-Hauser rearrangement products
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Selective amine de-alkylation enables the conversion of Sommelet-Hauser rearrangement products into 2-aryl-2-bromoacetic acid derivatives. These compounds are valuable synthetic intermediates in the synthesis of α-aryl-α-amino or α-aryl-β-amino acid deriv
- Tayama, Eiji,Sato, Ryota,Takedachi, Keisuke,Iwamoto, Hajime,Hasegawa, Eietsu
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experimental part
p. 4710 - 4718
(2012/07/28)
-
- Treatment of alcohols with tosyl chloride does not always lead to the formation of tosylates
-
Treatment of substituted benzyl alcohols with tosyl chloride resulted in the formation of the corresponding chlorides, not the usual tosylates. A series of experiments demonstrated that it was possible to predict whether chlorination or tosylation would occur for substituted benzyl alcohols and pyridine methanols. Treatment of electron withdrawing group-substituted benzyl alcohols with tosyl chloride gave the corresponding chlorides in moderate yields under mild conditions, which provided a simple way to directly prepare chlorides from alcohols.
- Ding, Rui,He, Yong,Wang, Xiao,Xu, Jingli,Chen, Yurong,Feng, Man,Qi, Chuanmin
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experimental part
p. 5665 - 5673
(2011/09/20)
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- Catalytic asymmetric α-chlorination of 3-acyloxazolidin-2-one with a trinary catalytic system
-
Direct asymmetric α-chlorination of aryl acetic acid derivatives was achieved with a novel trinary activation system consisting of a catalytic amount of NiCl2/(R)-BINAP, Et3SiOTf, and a tertiary amine base. The reaction smoothly affo
- Hamashima, Yoshitaka,Nagi, Tatsuya,Shimizu, Ryo,Tsuchimoto, Teruhisa,Sodeoka, Mikiko
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scheme or table
p. 3675 - 3678
(2011/09/15)
-
- Aromatic cation activation of alcohols: Conversion to alkyl chlorides using dichlorodiphenylcyclopropene
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(Chemical Equation Presented) A novel paradigm for the activation of alcohols toward nucleophilic displacement via formation of cyclopropenium ethers is described. The conversion of a range of alcohol substrates to the corresponding alkyl chlorides occurs rapidly upon treatment with 3,3-dichloro-1,2-diphenylcyclopropene. 1H NMR data support the intermediacy of a cyclopropenium intermediate, and the reaction is demonstrated to proceed primarily via the SN2 mechanism for 1-phenylethanol. A total of 12 examples of substrate scope are provided.
- Kelly, Brendan D.,Lambert, Tristan H.
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supporting information; experimental part
p. 13930 - 13931
(2009/12/25)
-
- Scandium triflate catalyzed transesterification of carboxylic esters
-
The direct transesterification of carboxylic esters is efficiently catalyzed with Sc(OTf)3 (10 mol%) in boiling alcoholic solvent. Methyl, ethyl, isopropyl, and allyl esters were prepared from a broad range of different substrates in high yields. The application of microwave irradiation led to significantly reduced reaction times. Georg Thieme Verlag Stuttgart.
- Remme, Nicole,Koschek, Katharina,Schneider, Christoph
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p. 491 - 493
(2007/12/27)
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- Dihydrobenzothiophenes
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Compounds of the formula (I) in which W, R1, R2, R3, R4, and q have the meanings indicated in Claim 1, can be employed, inter alia, for the treatment of tumours.
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-
-
- An unexpected synthesis of ketene monothioacetals
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Some dithiocarbonates (xanthates) can be converted into ketene monothioacetals through extrusion of sulfur upon treatment with base and an alkylating agent. The Royal Society of Chemistry.
- Fabre, Stephanie,Vila, Xavier,Zard, Samir Z.
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p. 4964 - 4966
(2007/10/03)
-
- DIHYDROBENZOTHIOPHENES
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The invention relates to compounds of formula (I), in which W, R1, R2, R3, R4, and q are defined as cited in claim 1. One application for said compounds is the treatment of tumours.
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Page/Page column 75-76
(2010/02/14)
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- Enzymatic hydrolysis and selective racemisation reactions of α-chloro esters
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The kinetic resolution of α-chloro esters was effected with good selectivity using CLEC (Cross-Linked Enzyme Crystals) enzymes. The selective racemisation of α-chloro esters in the presence of α-chloro acids enabled a successful dynamic kinetic resolution reaction to be performed.
- Haughton, Louise,Williams, Jonathan M. J.
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p. 943 - 946
(2007/10/03)
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- Thionyl chloride-benzotriazole in methylene chloride: A convenient solution for conversion of alcohols and carboxylic acids expeditiously into alkyl chlorides and acid chlorides by simple titration
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A solution of 1:1 equivalent of thionyl chloride and benzotriazole in dry methylene chloride efficiently transforms alcohols and carboxylic acids into the corresponding alkyl chlorides and acid chlorides respectively at room temperature, with excellent yields by simple titration.
- Chaudhari, Sachin S.,Akamanchi, Krishnacharya G.
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p. 1763 - 1765
(2007/10/03)
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- Reactions of perfluoroalkanesulfonyl chlorides with silyl enol ethers catalyzed by a ruthenium(II) phosphine complex
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Reactions of trifluoromethane- and tridecafluorohexanesulfonyl chlorides with silyl enol ethers have been investigated in the presence of a ruthenium(II) phosphine complex. Perfluoroalkylation and chlorination occurred depending on the substituent of silyl enol ether; i.e. perfluoroalkylated compound was selectively obtained in the reactions with silyl enol ether possessing an electron-withdrawing group, on the other hand, chlorinated compounds selectively formed in the reaction with a silyl enol ether possessing electron-donating group.
- Kamigata, Nobumasa,Udodaira, Kumiko,Shimizu, Toshio
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p. 155 - 168
(2007/10/03)
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- Enantioselective Protonation of Ketene Bis(trimethylsilyl) Acetals Derived from α-Aryl-α-haloacetic Acids Using LBA
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Optically active α-halocarboxylic acids and derivatives are important and versatile building blocks in organic synthesis. Lewis acid assisted chiral Bronsted acid (LBA) was recently prepared in situ from tin(IV) tetrachloride and optically pure binaphthol
- Ishihara, Kazuaki,Nakamura, Shingo,Yamamoto, Hisashi
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p. 513 - 517
(2007/10/03)
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- Effect of fluorine substitution of α-and β-hydrogen atoms in ethyl phenylacetate and phenylpropionate on their stereoselective hydrolysis by cultured cancer cells
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(±)-Ethyl 2-fluoro-2-phenylacetate was stereoselectively hydrolyzed by cultured cells of several rat cancer cell lines to give the carboxylic acid rich in the R enantiomer. The stereoselectivity increased for (±)-ethyl 2-fluoro-2-phenylpropionate (2b) with all present cell lines and for (±)-ethyl 2-phenyl-3,3,3-trifluoropropionate (3b) with rat hepatoma McA-RH7777 cell line. The stereoselectivity was different for the different cell lines, as McA-RH7777 cells preferred (R)-2b in contrast with the preference towards (S)-2b by other cells such as ras oncogene-transformed rat liver Anr4 cells. These stereoselectivities were different from those for non-fluorinated (±)-ethyl 2-phenylpropionate. Thus fluorine atoms are recognized by ester hydrolases of cancer cells, and fluorine substitution on the acyl group will be useful for making ester-type anticancer prodrugs more specific to cancer cells.
- Yamazaki, Yoshimitsu,Yusa, Shiro,Kageyama, Yu-Ichi,Tsue, Hirohito,Hirao, Ken-Ichi,Okuno, Hiroaki
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p. 167 - 171
(2007/10/03)
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- Trichloroisocyanuric Acid Oxidation of 2-Chloro Aldehyde Acetals to 2-Chloro Acids Esters
-
2-Chloro acid methyl esters were prepared in good yields treating 2-chloro aldehyde dimethyl acetals with trichloroisocyanuric acid in DMF.Aldehyde dimethyl acetals with the 2-halogen on a tertiary carbon atom were poorly reactive and could be oxidized efficiently only after their transformation into 1,3-dioxolanes.
- Boni, Monica,Ghelfi, Franco,Pagnoni, Ugo Maria,Pinetti, Adriano
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p. 156 - 159
(2007/10/02)
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- Novel Photocycloadditions of Electron-Deficient Nitrones to 2-Methyl-2-butene
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In order to decrease the ground state reactivity and increase their potential for cycloadditions, cyano- and methoxycarbonyl-substituted nitrones 1a and 1b, respectively, were prepared and irradiated in the presence of electron-rich alkenes such as 2 to afford the corresponding oxazolidines in which the oxygen atom becomes attached to the least substituted terminus of the olefin and nitrogen attaches the more highly substituted counterpart.While the oxazolidines 12a and 12b obtained from 1b, via the intermediacy of oxaziridine(s) 15 and subsequent N-O bond scission, are isolated and characterized, the oxazolidine(s) 18 formed by cycl ization of 1a are more labile and may undergo ionization to the stabilized oxazolinium ion 19 followed by nucleophilic attack by cyanide ion with accompanying ring opening to afford 6.A sequential diradical mechanism is proposed to rationalize the formation of the observed photoproducts 5 and 6.
- Sehgal, R. K.,Griffin, G. W.
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p. 513 - 517
(2007/10/02)
-
- Conversion of Aromatic Ketones into α-Arylalkanoic Acids. Part 2. Routes Employing Peracid, Chlorine, or Nitrous Acid
-
Further methods for effecting the oxidative rearrangement of 1-arylalkanones to α-arylalkanoic esters have been investigated.It has been shown that appropriate α-iodoacetals, readily prepared from the ketones, can be converted into esters on treatment either with a peracid or with chlorine.Using the latter reagent, α-chlorination of the ester can be an unwanted side reaction with some substrates and the factors governing by-product formation are discussed.It is demonstrated that, employing chlorine, the process can be made catalytic in iodine.The acetals of 2-amino-1-arylalkanones have also been shown to give high yields of esters under diazotising conditions adding support to the suggestion that the ion, ArC(OR)2CHR', or an incipient version of the ion, is a key intermediate in the process.
- Higgins, Stanley D.,Thomas, C. Barry
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p. 1483 - 1488
(2007/10/02)
-
- Conversion of Aromatic Ketones into α-Arylalkanoic Acids. Oxidation by Thallium(III) and by Halogens
-
The mechanism by which thallium (III) nitrate oxidises aromatic ketones to α-arylalkanoic acids has been investigated and the role of additives in the system elucidated.It is found that in the absence of additives an organothallium intermediate, most probably the phenacylthallium species BzCH2Tl(NO3)2, persists and that the key to an efficient rearrangement is the ready conversion of this compound into its acetal.Thallium(III) is shown not to be a unique reagent for the oxidation.Other oxidants capable of acting initially as an electrophile and then as a leaving group are equally effective, provided that formation of an acetal is possible.Iodine-silver nitrate in particular offers considerable advantages as reagent over thallium(III).Higher specificity is achieved, unwanted side-reactions can be avoided, and toxicity problems are eliminated.Bromine may be used instead of iodine, but chlorine proves unsatisfactory as an oxidant.
- Higgins, Stanley D.,Thomas, Barry C.
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p. 235 - 242
(2007/10/02)
-
- Method of preparing arylacetic acid alkyl esters
-
In a process of producing an alkyl ester of a substituted or unsubstituted arylacetic acid wherein a substituted or unsubstituted aromatic halogen methyl compound is reacted with carbon monoxide and an alcohol having an alkoxy group the same as that of said ester, the improvement which comprises carrying out said reaction in a basic reaction medium in the presence as catalyst of: A. cobalt salt, metal or metal alloy and a sulfur compound, or B. a metal carbonyl compound.
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