85515-85-1Relevant academic research and scientific papers
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.
Continuous flow synthesis of toxic ethyl diazoacetate for utilization in an integrated microfluidic system
Maurya, Ram Awatar,Min, Kyoung-Ik,Kim, Dong-Pyo
supporting information, p. 116 - 120 (2014/01/06)
An integrated microfluidic system for multiple reactions and separations of hazardous ethyl diazoacetate is presented. The integrated techniques include: a droplet technique for liquid-liquid and/or gas-liquid separation and in situ generation of the toxic reagent, a dual channel membrane technique based on a cheap polymeric microseparator for liquid-liquid separation, and a capillary microreactor for carrying out cascade reactions in a sequential and continuous manner.
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.
Development of the enantioselective addition of ethyl diazoacetate to aldehydes: Asymmetric synthesis of 1,2-diols
Trost, Barry M.,Malhotra, Sushant,Koschker, Philipp,Ellerbrock, Pascal
supporting information; experimental part, p. 2075 - 2084 (2012/03/12)
A novel synthetic strategy toward the asymmetric synthesis of vicinal diols bearing a tertiary center is presented. The method encompasses the dinuclear Mg-catalyzed asymmetric addition of ethyl diazoacetate into several aldehydes, oxidation of the diazo functionality, and diastereoselective alkyl transfer of various organometallics into the resulting chiral β-hydroxy-α- ketoesters to afford a diverse range of 1,2-diols in high yield, diastereoselectivity, and chirality transfer.
Catalysis in water: Aldol-type reaction of aldehydes and imines with ethyl diazoacetate catalyzed by highly basic magnesium/lanthanum mixed oxide
Kantam, M. Lakshmi,Balasubrahmanyam,Kumar, K. B. Shiva,Venkanna,Figueras
, p. 1887 - 1890 (2008/09/17)
Magnesium/lanthanum mixed oxide is an effective heterogeneous catalyst for aldol-type condensation of aldehydes and imines with ethyl diazoacetate (EDA) at room temperature in water to afford corresponding β-hydroxy-α-diazo carbonyl compounds and β-amino-α-diazo carbonyl compounds in good yields. The catalyst is recovered and reused for several cycles with consistent activity.
DBU-promoted condensation of acyldiazomethanes to aldehydes and imines under catalytic conditions
Jiang, Nan,Wang, Jianbo
, p. 1285 - 1287 (2007/10/03)
The condensation of acyldiazomethanes to aldehydes and imines can be promoted with catalytic amount of DBU. The condensation gives β-hydroxy α-diazo carbonyl compounds or β-amino α-diazo carbonyl compounds in high yields.
Fluoride-catalyzed aldol reaction of ethyl trimethylsilyldiazoacetate with aldehydes leading to ethyl α-diazo-β-hydroxy esters and rhodium catalyzed decarboxylative rearrangement of diazo urethanes leading to β- amino acrylates
Kanemasa, Shuji,Araki, Takahiro,Kanai, Toshio,Wada, Eiji
, p. 5059 - 5062 (2007/10/03)
Ethyl trimethylsilyldiazoacetate reacts smoothly with a variety of aldehydes at 0 °C in the presence of a catalytic amount of tetrabutylammonium fluoride to produce α-diazo-β-hydroxy esters in good to excellent yields. The resulting α-diazo-β-hydroxy esters can be stereoselectively transformed, by a sequence of carbamation with p- toluenesulfonyl isocyanate and rhodium(II)-induced decarboxylative rearrangement, to α- or β-substituted β-(p-toluenesulfonylamino)acrylates depending upon migration aptitude of the substituents derived from the aldehydes.
