144713-04-2Relevant academic research and scientific papers
Gold-Catalyzed 1,2-Acyloxy Migration/Coupling Cascade of Propargyl Diazoacetates: Synthesis of Isomycin Derivatives
Bao, Ming,Wang, Xin,Qiu, Lihua,Hu, Wenhao,Hong Chan, Philip Wai,Xu, Xinfang
supporting information, (2019/03/19)
An efficient gold(I)-catalyzed carbocyclization reaction for the synthesis of isomycin derivatives from propargyl diazoacetates has been developed. The suggested cyclization pathway delineated the first example of a vinyl gold carbenoid species generated in situ from gold(I)-catalyzed 1,2-acyloxy migration and intercepted by a cross-coupling reaction with the remaining tethered diazo functionality. The use of protic additives was essential to regulating the reaction outcome by fine-tuning the catalytic preference of the gold(I) complex.
Gold(I)-Catalyzed and H2O-Mediated Carbene Cascade Reaction of Propargyl Diazoacetates: Furan Synthesis and Mechanistic Insights
Bao, Ming,Qian, Yu,Su, Han,Wu, Bing,Qiu, Lihua,Hu, Wenhao,Xu, Xinfang
supporting information, p. 5332 - 5335 (2018/09/13)
A novel gold-catalyzed water-mediated carbene cascade reaction of propargyl diazoacetates has been developed. Mechanistic investigation indicates that this reaction is initiated by gold-catalyzed gold-carbene formation followed by an unprecedented 6-endo-
Regio- And stereoselective synthesis of fluoroalkenes by Directed Au(I) catalysis
Gorske, Benjamin C.,Mbofana, Curren T.,Miller, Scott J.
supporting information; experimental part, p. 4318 - 4321 (2009/12/26)
Au-catalyzed hydrofluorlnation reactions of a range of functionalized alkynes are reported. In the presence of an appropriate directing group, localized with particular spacing from the pendant alkyne, regloselectlve and predictable conversion of the alky
Spectroscopy and photochemistry of phenylacetic acid esters and related substrates. The stereoelectronic dependence of the aryl/carboxyl bichromophore interaction
Kasper,Nash,Morrison
, p. 2792 - 2798 (2007/10/02)
The 254-nm-initiated Norrish Type II photofragmentation of the ethoxyethyl esters of a series of phenylacetic acids (1b-4b) has been studied in order to further elaborate the aryl/ester interaction that is photochemically and photophysically evident in these systems. The ethoxyethyl ester of benzonorbornene-1-carboxylic acid (5) has also been prepared and studied, as has a rigid tricyclic lactone (6) which places the chromophores in an optimal stereoelectronic relationship for interaction. The experimental work is accompanied by Hartree-Fock (HF), Natural Bond Orbital (NBO), and Configuration Interaction with Single Excitations (CIS) calculations on the methyl esters of phenylacetic acid (1a) and α-methoxyphenylacetic acid (4a). The calculations confirm extensive through-space (TS) and through-bond (TB) interactions between the aryl and ester π* orbitals but fail to provide conformational or electronic arguments to explain the unusually high reactivity of the α-methoxy series.
Rhodium(II)-Catalyzed Cyclization of 2-Alkynyl 2-Diazo-3-oxobutanoates as a Method for Synthesizing Substituted Furans
Pawda, Albert,Kinder, Frederick R.
, p. 21 - 28 (2007/10/02)
A series of 2-alkynyl 2-diazo-3-oxobutanoates, when treated with a catalytic quantity of rhodium(II) acetate, were found to produce furofurans in good yield.The reaction proceeds by addition of a rhodium-stabilized carbenoid onto the acetylenic ?-b
