77252-94-9Relevant academic research and scientific papers
Efficient preparation of α-ketoacetals
Ayala-Mata, Francisco,Barrera-Mendoza, Citlalli,Jimenez-Vazquez, Hugo A.,Vargas-Diaz, Elena,Zepeda, L. Gerardo
, p. 13864 - 13878 (2013/03/13)
The Weinreb amides 2a,b were prepared from the a,a-dimethoxyacetic acids 1c,d. A number of representative nucleophilic additions (RMgX and RLi) on 2 afforded a-ketoacetals 3a-j in 70-99% yield. These compounds represent a versatile arrangement of functional groups of significant synthetic value, as demonstrated in the synthesis of (±)-salbutamol.
Selective protection of the functionalities of α-hydroxy unsaturated aldehydes
Khamliche,Bakkas,Robert
, p. 1129 - 1131 (2007/10/02)
The polyfunctionalized title compounds α-enol aldehydes are selectively protected either as ethylenic aldehyde acetates, ethylenic aldehyde sulfonates, ethylenic acetal sulfonates, or oxo acetal derivatives.
Selenium-Mediated Conversion of Alkynes into α-Dicarbonyl Compounds
Tiecco, Marcello,Testaferri, Lorenzo,Tingoli, Marco,Chianelli, Donatella,Bartoli, Donatella
, p. 4529 - 4534 (2007/10/02)
The reaction of terminal and internal alkynes with diphenyl diselenide and ammonium peroxydisulfate in methanol proceeds smoothly to give α-keto acetals and α-keto ketals, respectively.This one-pot procedure is suggested to proceed through the initial formation of phenylselenenyl sulfate, a strong electrophilic reagent which effects the methoxyselenenylation of the alkynes.The addition products thus formed suffer methoxydeselenenylation giving the observed products and regenerating the phenylselenenylating agent.In some cases the reaction can be carried out using only catalytic amounts of diphenyl diselenide.The same reaction carried out in the presence of water or of ethylene glycol gives the unprotected or the diprotected α-dicarbonyl compounds, respectively.
Kinetic and mechanistic studies on the rearrangement of 1-(substituted phenyl)-1,3-dimethoxy-2-propanones
Chen,Li,Zhang
, p. 169 - 177 (2007/10/02)
The mechanism of rearrangement of 1-(substituted phenyl)-1,3-dimethoxy-2-propanones to give substituted benzylglyoxal dimethyl acetals (5) was studied by kinetic measurements, by the effects of acid catalysis, by rearrangements in the absence of acid and
A Study of Rearrangement of some 1,3-Dimethoxyalkan-2-ones
Yu, Yin,Chen, Guo-qiang,Zhu, Jun,Zhang, Xu-sheng,Chen, Shu-xin,et al.
, p. 2239 - 2243 (2007/10/02)
1,3-Dialkoxyacetones, 1-alkyl- and 1-(substituted phenyl)-, 1-alkanoyl-1,3-dimethoxyacetones, and methyl 2,4-dimethoxyacetoacetate were shown to undergo acid-catalysed rearrangement to give respectively methylglyoxal dialkyl acetals, 3-substituted methylglyoxal dimethyl acetals, 5-alkyl-3-methoxy- and 4,5-dimethoxyfuran-2(5H)-ones. 1-(Substituted aroyl)-1,3-dimethoxyacetones underwent only scission to give substituted ω-methoxyacetophenones.Methyl 2-alkyl-2,4-dimethoxyacetoacetates, 3- and 1-methoxy-, and 1,5-dimethoxypentane-2,4-diones were not affected by similaracid treatment except for the fact that they suffered some limited C-C bond scissions.Implications related to rearrangement mechanisms are discussed.
