27262-59-5Relevant articles and documents
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.
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.
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.
