42411-55-2Relevant academic research and scientific papers
Efficient α-chlorination of carbonyl containing compounds under basic conditions using methyl chlorosulfate
Silva, Saúl,Maycock, Christopher D.
supporting information, p. 1233 - 1238 (2018/02/27)
An efficient method for the α-chlorination of ketones under basic conditions is described using methyl chlorosulfate. Its applicability for the chlorination of other functional groups has also been studied and it is equally useful for the synthesis of α-chloroesters and amides. Methyl chlorosulfate is described for the first time as a positive chlorine source. Some aldol reactions which occur during the chlorination of some substrates are also reported.
Preparation method of 3-aminomethyl tetrahydrofuran
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Paragraph 0022-0024, (2017/07/12)
The invention relates to a preparation method of 3-aminomethyl tetrahydrofuran. Specifically the invention relates to a method of preparing 3-aminomethyl tetrahydrofuran through reducing 3-cyanotetrahydrofuran. A novel synthesis technology is adopted; gamma-butyrolactone and a halogen simple substance X2 are taken as the raw materials to prepare 3-X-gamma-butyrolactone; then 3-X-gamma-butyrolactone is reduced by a reducing agent to obtain 2-X-1,4-butylene glycol; 2-X-1,4-butylene glycol is dehydrated by a dehydrating agent to obtain 3-X tetrahydrofuran; 3-X tetrahydrofuran is converted into 3-cyanotetrahydrofuran in the presence of a cyaniding catalyst, and finally 3-cyanotetrahydrofuran is converted into 3-aminomethyl tetrahydrofuran in the presence of a hydrogenation catalyst. The synthesis technology has the advantages of easily available raw materials, simple operation, mild reaction conditions, high yield and product purity, little environmental pollution, and low production cost, is suitable for industrial massive production, and has a wide application prospect.
Asymmetric suzuki cross-couplings of activated secondary alkyl electrophiles: Arylations of racemic α-chloroamides
Lundin, Pamela M.,Fu, Gregory C.
supporting information; experimental part, p. 11027 - 11029 (2010/09/17)
A nickel-catalyzed stereoconvergent method for the enantioselective Suzuki arylation of racemic α-chloroamides has been developed. This process provides a unique example of an asymmetric arylation of an α-haloamide, an enantioselective arylation of an α-chlorocarbonyl compound, and an asymmetric Suzuki reaction with an activated alkyl electrophile or an arylboron reagent. The method is also applicable to the corresponding enantioselective cross-coupling of α-bromoamides. The coupling products can be transformed without racemization into enantioenriched α-arylcarboxylic acids and primary alcohols. A modest kinetic resolution of the α-chloroamide was observed; a mechanistic study indicated that the selectivity may reflect discrimination by the chiral catalyst of the two enantiomeric α-chloroamides in an irreversible oxidative-addition process.
An unusual conformation of α-haloamides due to cooperative binding with zincated porphyrins
Tanasova, Marina,Yang, Qifei,Olmsted, Courtney C.,Vasileiou, Chrysoula,Li, Xiaoyong,Anyika, Mercy,Borhan, Babak
supporting information; experimental part, p. 4242 - 4253 (2011/02/25)
CD and NMR spectroscopic evidence of cooperative binding between an α-halogen atom and a carboxamide group with a zinc porphyrin leads to an unprecedented conformation for the determination of the absolute stereochemistry of α-haloamides (α-halocarboxylic acids derivatized with 1,4-phenylenediamine) through the use of exciton-coupled circular dichroism (ECCD). With the use of chiral lactams, whose rotomeric contributions are minimized, both ECCD and NMR spectroscopy demonstrate that the porphyrin favors binding to the side of the sterically more demanding halogen atom as compared to the smaller hydrogen atom. In all, the data is strongly suggestive of an unusual conformation not observed before for α-chiral amides. A mnemonic for determining the absolute stereochemistry of α-halogenated carboxylic acids is provided.
Method for the Production of D,L-2-Hydroxy-4-Alkylthio Butyric Acid
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Page/Page column 4-5, (2009/12/28)
The present invention relates to a process for preparing compounds of the formula (I) by reacting compounds of the formula (II) with thiolates (RS)nM. The present invention further relates to a process for preparing compounds of the formula (II) from γ-butyrolactone.
Reactions of α-chloro β-oxo aldehydes with CH-acid anions
Guseinov, F. I.
, p. 743 - 745 (2007/10/03)
The reactions of α-chloro and α,α-dichloro β-oxo aldehydes with carbanions are accompanied by the cleavage of the carbon-carbon bond in the chloro aldehydes and result in formylation of CH-acids. These electrophiles react with carbanions, which are generated in situ from CH-acids in the presence of AcONa in aprotic solvents, to form polyfunctional hydroxy compounds.
Reactions of α-Chloro-β-oxoaldehydes with Dialkyl Phosphites
Guseinov,Burangulova,Moskva
, p. 1564 - 1567 (2007/10/03)
Sodium dialkyl phosphites react with α-chloro- and α,α-dichloro-β-oxoaldehydes exclusively at the aldehyde carbonyl group with rupture of the C-CHO bond. The primary products are corresponding α-chloro- and α,α-dichloroenolates and unstable phosphinoylformaldehydes; the latter decompose into dialkyl hydrogen phosphites and carbon monoxide. Condensation products of α-halo-β-oxoaldehydes with dialkyl hydrogen phosphites in the presence of sodium hydride undergo similar transformations.
Reactions of α-Chloro- and α,α-dichloro-β-oxoaldehydes with Anionic Nucleophiles
Guseinov, F. I.,Tagiev, S. Sh.,Moskva, V. V.
, p. 86 - 89 (2007/10/03)
The reaction of α-chloro and α,α-dichloro-β-oxoaldehydes with anionic nucleophiles (NaOH, MeONa, PhONa, MeCOOK) proceeds mainly via haloform splitting with elimination of the formyl group; only with the most nucleophilic sodium methoxide, the reaction at the β-carbon atom partially occurs.The intermediate anions react with benzaldehyde to give difficulty accessible polyfunctional compounds.
