83190-30-1Relevant academic research and scientific papers
Site-selective synthesis of 1,3-dioxin-3-ones: Via a gold(i) catalyzed cascade reaction
An, Juzeng,Pedrazzani, Riccardo,Monari, Magda,Marin-Luna, Marta,Lopez, Carlos Silva,Bandini, Marco
supporting information, p. 7734 - 7737 (2020/07/27)
A novel gold(i)-catalyzed protocol for the synthesis of 4H-1,3-dioxin-3-ones is presented. The protocol exploits a metal induced cascade sequence involving a [3,3]-sigmatropic rearrangement followed by regioselective O-annulation reactions. A wide range of oxygen-based heterocyclic scaffolds (21 examples) were achieved in excellent yield (up to 80percent) and a detailed computational investigation as well as deuterium-labelling investigations enabled all the plausible reaction pathways to be mapped and the rationalization of the recorded regioselectivity.
Bismuth(III) chloride-catalyzed highly efficient transesterification of β-keto esters
Sabitha, Gowravaram,Srinivas, Rangavajjula,Gopal, Peddabuddi,Bhikshapathi,Yadav, Jhillu Singh
experimental part, p. 119 - 121 (2011/03/17)
Bismuth(III) chloride was found to be an efficient catalyst for the transesterification of a variety of β-keto esters with a wide range of alcohols to afford transesterified products in good to high yields in short reaction times (see Table). Copyright
Selective Catalytic Transesterification, Transthiolesterification, and Protection of Carbonyl Compounds over Natural Kaolinitic Clay
Ponde, Datta E.,Deshpande, Vishnu H.,Bulbule, Vivek J.,Sudalai, Ammugam,Gajare, Anil S.
, p. 1058 - 1063 (2007/10/03)
Transesterification and transthiolesterification of β-keto esters with variety of alcohols and thiols and selective protection of carbonyl functions with various protecting groups catalyzed by natural kaolinitic clay are described. The clay has been found to be an efficient catalyst in transesterifying long chain alcohols, unsaturated alcohols, and phenols to give their corresponding β-keto esters in high yields. For the first time, transthiolesterification of β-keto esters with a variety of thiols has been achieved under catalytic conditions. Clay also catalyzes selective transesterification of β-keto esters by primary alcohols in the presence of secondary and tertiary alcohols giving corresponding β-keto esters. A systematic study involving the reactivity of different nucleophiles (alcohols, amines, and thiols) toward β-keto esters is also described. Sterically hindered carbonyl groups as well as α,β-unsaturated carbonyl groups underwent protection without the deconjugation of the double bond. Chemoselective protection of aldehydes in the presence of ketones has also been achieved over natural kaolinitic clay.
