4383-55-5Relevant academic research and scientific papers
DBU-catalyzed condensation of acyldiazomethanes to aldehydes in water and a new approach to ethyl β-hydroxy α-arylacrylates
Xiao, Fengping,Liu, Yu,Wang, Jianbo
, p. 1147 - 1149 (2007/10/03)
DBU-catalyzed condensation of ethyl diazoacetate (EDA) with aldehydes in pure water afforded corresponding β-hydroxy α-diazo carbonyl compounds. The β-hydroxy group of the products was further converted into β-siloxy group. The Rh(II)-catalyzed reaction of the β-aryl β-siloxy α-diazo carbonyl compounds gave 1,2-aryl shift products predominantly. The three-step transformation constitutes an efficient synthesis of ethyl β-hydroxy α-arylacrylates.
Iron Lewis Acid Catalyzed Reactions of Aromatic Aldehydes with Ethyl Diazoacetate: Unprecedented Formation of 3-Hydroxy-2-arylacrylic Acid Ethyl Esters by a Unique 1,2-Aryl Shift
Mahmood, Syed J.,Hossain, M. Mahmun
, p. 3333 - 3336 (2007/10/03)
The iron Lewis acid [η5-(C5H5)Fe(CO)2(THF)]BF 4 (1) was found to catalyze reactions of ethyl diazoacetate (EDA) and aromatic aldehydes, yielding 3-hydroxy-2-arylacrylie acid ethyl esters and the corresponding β-keto esters. According to the literature, this is the first report of the formation of enol esters from EDA and aromatic aldehydes. The yield of the enol esters increased with electronrich aldehydes. With 2,4-dimethoxybenzaldehyde the only product isolated was the corresponding enol ester in 80% yield. However, in the presence of electron-deficient aldehydes such as p-nitrobenzaldehyde, formation of enol ester decreased to 32%. The most unique feature of these reactions is that enol esters are formed by an unusual 1,2-aryl shift, from a possible intermediate 8, which in turn is formed from the reaction of the iron aldehyde complex 7 and EDA.
