22609-91-2Relevant academic research and scientific papers
An efficient synthetic approach towards fully functionalized tetronic acids: The use of 1,3-dioxolane-2,4-diones as novel protected-activated synthons of α-hydroxy acids
Prousis, Kyriakos C.,Markopoulos, John,Mckee, Vickie,Igglessi-Markopoulou, Olga
, p. 8637 - 8648 (2015)
A new strategy for the synthesis of tetronic acids with control over the regioselective introduction of substituents at the C-5 position has been developed. The construction of the densely functionalized quaternary carbon center within these molecules is of great importance. The key element for the proposed protocol was the utilization of O-carboxyanhydrides (OCA's) of optically active α-hydroxy acids, as promising bidentate protective/activating precursors. The structure of the new compounds was investigated by using NMR spectral data and X-ray structural analyses.
Synthesis of tetronic acids from propargylic alcohols and CO2
Shen, Guo,Zhou, Wen-Jun,Zhang, Xiao-Bo,Cao, Guang-Mei,Zhang, Zhen,Ye, Jian-Heng,Liao, Li-Li,Li, Jing,Yu, Da-Gang
, p. 5610 - 5613 (2018)
A direct and practical synthesis of important tetronic acids from easily available propargylic alcohols and carbon dioxide is reported for the first time. This transition-metal-free transformation features high atom- and step-economy, mild reaction conditions, good functional group tolerance and high yield. Preliminary mechanistic studies suggest that the reaction proceeds via cyclization to give alkylidene cyclic carbonate, ring-opening and re-cyclization processes.
Esters as Radical Acceptors: β-NHC-Borylalkenyl Radicals Induce Lactonization by C?C Bond Formation/Cleavage on Esters
Shimoi, Masaki,Maeda, Katsuhiro,Geib, Steven J.,Curran, Dennis P.,Taniguchi, Tsuyoshi
, p. 6357 - 6361 (2019/04/13)
Substituted propargyl acetates are converted into 4-boryl-2(5H)-furanones upon thermolysis in the presence of an N-heterocyclic carbene borane (NHC-borane) and di-tert-butyl peroxide. The acetyl methyl group is lost during the reaction as methane. Evidence suggests that the reaction proceeds by a sequence of radical events including: 1) addition of an NHC-boryl radical to the triple bond; 2) cyclization of the resultant β-borylalkenyl radical to the ester carbonyl group; 3) β-scission of the so-formed alkoxy radical to provide the 4-boryl-2(5H)-furanone and a methyl radical; and 4) hydrogen abstraction from the NHC-borane to return the initial NHC-boryl radical and methane.
