87228-44-2Relevant articles and documents
Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group**
Ciofini, Ilaria,Force, Guillaume,Leb?uf, David,Mayer, Robert J.,Perfetto, Anna
supporting information, p. 19843 - 19851 (2021/08/13)
Macrolactones constitute a privileged class of natural and synthetic products with a broad range of applications in the fine chemicals and pharmaceutical industry. Despite all the progress made towards their synthesis, notably from seco-acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe a strategy that relies on the formation of a mixed anhydride incorporating a pentafluorophenyl group which, due to its high electronic activation enables a convenient access to macrolactones, macrodiolides and esters with a broad versatility. Kinetic studies and DFT computations were performed to rationalize the reactivity of the pentafluorophenyl group in macrolactonization reactions.
2,6-Dimethyl-4-nitrobenzoic anhydride (DMNBA): An effective coupling reagent for the synthesis of carboxylic esters and lactones
Shiina, Isamu,Miyao, Ryo
experimental part, p. 1313 - 1328 (2009/07/05)
Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2,6-dimethyl-4-nitrobenzoic anhydride with triethylamine by the promotion of 4-(dimethylamino)pyridine. The efficiency of the esterification is compared to those of other dehydrations using substituted benzoic anhydrides as coupling reagents. This method was successfully applied to the synthesis of threo-aleuritic acid lactone and the desired 17-membered ring compound was prepared in high yield at room temperature from the corresponding free trihydroxycarboxylic acid using 2,6-dimethyl-4-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine.
A mild and efficient chemoselective protection of primary alcohols as pivaloyl esters using La(NO3)3·6H2O as a catalyst under solvent-free conditions
Prabhakar,Suryakiran,Venkateswarlu
, p. 732 - 733 (2008/02/09)
Primary alcohols are selectively and efficiently protected as their pivaloyl esters with pivaloyl chloride in the presence of catalytic amounts of La(NO3)3·6H2O at room temperature under solvent-free conditions in excellent yields. Copyright
