We present a general model for understanding the stereochemical course of intramolecular Michael reactions. We show that the addition of β-ketoester enolates to α,β-unsaturated esters and imides bearing adjacent stereocenters (X, Y = H, Me, OR) leads to high levels of asymmetric induction. Reinforcing and nonreinforcing stereochemical relationships are evaluated from the syn and anti reactant d...

The synthesis and properties of multifunctional thioureas bearing a variety of functional groups at a position remote from the thiourea moiety are described. A 1,5-disubstituted triazole tether connected with a thiourea and another functional group was synthesized via ruthenium catalyzed Huisgen cycloaddition. We demonstrate the utility of the synthetic thioureas as asymmetric catalysts and pro...

Perylene bisimides (PBIs) self-assemble in solution. The solubility of the PBIs is commonly changed through the choice of substituents at the imide positions. It is generally assumed this substitution does not affect the electronic properties of the PBI, and that the properties of the self-assembled aggregate are essentially that of the isolated molecule. However, substituents do affect the sel...

a Laboratory of Environmental Science and Technology, Xinjiang Technical Institute of Physics and Chemistry, Key Laboratory of Functional Materials and Devices for Special Environments, Chinese Academy of Sciences, Urumqi 830011, People’s Republic of China University of Chinese Academy of Sciences, Beijing 100049, People’s Republic of China Nano Institute of Utah and Department of Materials Sci...

A new photoactive polymer comprising benzo[1,2-b:3,4-b':5,6-d']trithiophene and 2,1,3-benzothiadiazole-5,6-dicarboxylic imide is reported. The synthetic design allows for alkyl chains to be introduced on both electron-rich and electron-deficient components, which in turn allows for rapid optimization of the alkyl chain substitution pattern. Consequently, the optimized polymer shows a maximum ef...

This study investigates thermophilic imidase activity of the liver. We demonstrate that imidase catalyzes the hydrolysis of imides at a temperature substantially higher than that of its native environment. Then, a thermophilic imidase is purified to homogeneity from pig liver, and its thermoproperties are studied. About 2500-fold of purification and 15% yield of imidase activity are obtained af...

Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming ...

A method for direct carbonylation of aminoquinoline benzamides has been developed. Reactions proceed at room temperature in trifluoroethanol solvent, use oxygen from air as an oxidant, and require Mn(OAc)3 as a cocatalyst. Benzoic and acrylic acid derivatives can be carbonylated by carbon monoxide affording imides in good yields. Halogen, nitro, ether, cyano, and ester functional groups are tol...

An efficient metal-free oxidative arylsulfonylation of α,β-unsaturated imides with sulfonylhydrazides leading to isoquinoline-1,3(2H,4H)-dione derivatives has been developed. The procedure involves the generation of sulfonyl radicals via cleavage of the S-N bond of sulfonylhydrazides with sulfonylation and C-H functionalization. The protocol uses the economical and environmentally friendly TBAI...

Eeny, meeny, miny ... enaminones! Lactams and imides have been shown to consistently provide enantioselectivities substantially higher than other substrate classes previously investigated in the palladium-catalyzed asymmetric decarboxylative allylic alkylation. Several new substrates have been designed to probe the contributions of electronic, steric, and stereoelectronic factors that distingui...