27262-59-5Relevant academic research and scientific papers
One-pot synthesis of α-diazo-β-hydroxyesters under phase-transfer catalysis and application to the catalytic asymmetric aldol reaction
Arai, Shigeru,Hasegawa, Kazuya,Nishida, Atsushi
, p. 1023 - 1026 (2004)
The one-pot (three steps) synthesis of α-diazo-β-hydroxyesters from tosyl chloride under phase-transfer catalysis is described. The catalytic asymmetric aldol reaction between a diazoester and aldehydes was also investigated and gave moderate to good enantioselectivity.
Stereoselective bioreduction of α-diazo-β-keto esters
Costin, Taíssa A.,González-Granda, Sergio,Gotor-Fernández, Vicente,Sá, Marcus M.
, (2020/02/28)
Diazo compounds are versatile reagents in chemical synthesis and biology due to the tunable reactivity of the diazo functionality and its compatibility with living systems. Much effort has been made in recent years to explore their accessibility and synth
Photocatalytic Alkylation of Pyrroles and Indoles with α-Diazo Esters
Ciszewski, Lukasz W.,Durka, Jakub,Gryko, Dorota
supporting information, p. 7028 - 7032 (2019/09/12)
This article describes the photoalkylation of electron-rich aromatic compounds with diazo esters. C-2-alkylated indoles and pyrroles are obtained with good yields even though the photocatalyst loading is as low as 0.075 mol %. For EWG-substituted substrates, the addition of a catalytic amount of N,N-dimethyl-4-methoxyaniline is required. Both EWG-EWG- and EWG-EDG-substituted diazo esters are suitable as alkylating agents. The reaction selectivity and mechanistic experiments suggest that carbenes/carbenoid intermediates are not involved in the reaction pathway.
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.
Deep eutectic solvent (DES) as dual solvent/catalyst for synthesis of α-diazocarbonyl compounds using aldol-type coupling
Miraki, Maryam Kazemi,Mehraban, Jamshid Azarnia,Yazdani, Elahe,Heydari, Akbar
, p. 129 - 132 (2017/04/01)
Deep eutectic solvent (DES) was employed as dual solvent/catalyst in the green synthesis of α-diazocarbonyl compounds using aldol-type coupling. α-Diazocarbonyl compounds are important synthetic intermediates with useful application for synthesis of amino alcohols and acids and many natural products. Moreover, the method is environmentally friendly because of avoidance of toxic solvents or hazardous catalysts.
KF/Nano-clinoptilolite Catalyzed Aldol-Type Reaction of Aldehydes with Ethyl Diazoacetate
Balou, Javad,Khalilzadeh, Mohammad A.,Zareyee, Dariush
, p. 2612 - 2618 (2017/09/06)
Abstract: Potassium fluoride supported on nano-clinoptilolite (KF/CP NPs) was used as an excellent catalytic system for direct aldol-type condensation of aldehydes with ethyl diazoacetate under solvent-less conditions. A variety of α-diazo carbonyl derivatives were prepared in good to excellent yields in short reaction times. Graphical Abstract: [Figure not available: see fulltext.]
C6-selective direct alkylation of pyridones with diazo compounds under Rh(III)-catalyzed mild conditions
Das, Debapratim,Biswas, Aniruddha,Karmakar, Ujjwal,Chand, Santanu,Samanta, Rajarshi
, p. 842 - 848 (2016/02/18)
A Rh(III)-catalyzed highly efficient C6-alkylation of 2-pyridones has been achieved successfully with α-diazo carbonyl compounds. The developed method is simple, mild, and highly regioselective with a broad range of substrate scope. The regioselectivity is guided by the pyridyl substituent attached to the nitrogen center of the pyridone ring. The directing group can be easily removed, and the only formed byproduct is nitrogen. Furthermore, other similar heterocyclic scaffolds can also be functionalized regioselectively under the developed conditions.
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.
Safe generation and direct use of diazoesters in flow chemistry
Müller, Simon T. R.,Smith, Daniel,Hellier, Paul,Wirth, Thomas
, p. 871 - 875 (2014/04/03)
A safe and fast method for the production of β-hydroxy-α- diazoesters in continuous flow technology is described. The synthesis involves the formation of ethyl diazoacetate in situ and the addition to several aldehydes in a two-step continuous flow microreactor setup. Rhodium acetate catalyzes a subsequent 1,2-hydride shift to give access to β-keto esters in a three-step sequence. Georg Thieme Verlag Stuttgart · New York.
