211318-51-3Relevant articles and documents
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)
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.
Zinc derivative of ethyl diazoacetate in the synthesis of α-diazo-β- hydroxy esters
Moody, Christopher J.,Neil Morfitt
, p. 1039 - 1042 (1998)
Addition of diethylzinc to ethyl diazoacetate generates a zinc derivative which adds to aldehydes to give α-diazo-β hydroxy esters.
Highly efficient and chemoselective direct aldol reaction of acyldiazomethane with aldehydes promoted by MgI2 etherate
Qi, Weipeng,Xie, Xiaoqiang,Zhong, Tengjiang,Zhang, Xingxian
supporting information, p. 194 - 196 (2017/09/30)
Direct aldol condensation of various aromatic, heteroaromatic, α,β-unsaturated aldehydes and aliphatic aldehydes with acyldiazomethane was realized using MgI2 etherate (MgI2·(Et2O)n) as a promoter in the presence of diisopropyl amine (DIPEA) in excellent yields in a short time under mild conditions with high chemoselectivity. Iodide counterion, and a non-coordinating less ploar reaction media (i.e., CH2Cl2) are among the critical factors for this unique reactivity.
An efficient and convenient aldol addition of acyldiazomethane with aldehydes promoted by MgI2 etherate
Xie, Xiaoqiang,Qi, Weipeng,Sun, Xinzhe,Zhang, Xingxian
, p. 87 - 91 (2017/10/10)
The aldol addition of acyldiazomethane with aromatic aldehydes, vinyl aldehyde and aliphatic aldehydes was carried out efficiently in the presence of MgI2 etherate and iPr2EtN (DIPEA) using untreated reagent-grade CH2Cl2 under atmospheric conditions in good to excellent yields. Iodide counterion and a non-coordinating reaction media (i.e. CH2Cl2) are among the critical factors for the unique reactivity of this reaction system.
An efficient aldol-type reaction of ethyl diazoacetate with aldehydes promoted by MgI2 etherate
Zhong, Tengjiang,Wu, Tianpeng,Zhang, Xingxian
, p. 690 - 691 (2015/01/09)
The first example of the preparation of α-diazo-β-hydroxy esters by the aldol-type condensation of aldehydes with ethyl diazoacetate using Et3N as base in the presence of magnesium iodide etherate [MgI2.(Et2O)n] has been achieved in good to excellent yields at room temperature in CH2Cl2 in 15-30 min.