Herein we report an efficient organocatalyst for the multicomponent Hantzsch reaction under mild condition.The product easily isolated by simple filtration and catalyst can be recovered.
Six compounds including five proline derivatives have been prepared and tested as chiral organocatalysts for enantioselective aldol reactions and Michael additions. The enantiomeric excesses, which are highly dependen...Six compounds including five proline derivatives have been prepared and tested as chiral organocatalysts for enantioselective aldol reactions and Michael additions. The enantiomeric excesses, which are highly dependent on the molecular structure of catalysts as well as experimental conditions, have reached over 98%.展开更多
The backbone of D-glucosamine hydrochloride was fine-tuned and modified by protecting the hydroxyl groups. In order to reduce imines with trichlorosilane, the carbohydrate-derived organocatalysts were prepared and scr...The backbone of D-glucosamine hydrochloride was fine-tuned and modified by protecting the hydroxyl groups. In order to reduce imines with trichlorosilane, the carbohydrate-derived organocatalysts were prepared and screened. Methyl-4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyr anoside was found as the best catalyst. The reduction was proceeded under CHCl3 as solvent at 40?C, affording 68% - 94% yield.展开更多
Prolinamido-glycoside catalyzed asymmetric aldol reaction in aqueous media is reported. The reactions are rapid and highly stereoselective when water is used as solvent. The stereoselectivities were under influence of...Prolinamido-glycoside catalyzed asymmetric aldol reaction in aqueous media is reported. The reactions are rapid and highly stereoselective when water is used as solvent. The stereoselectivities were under influence of configurations of a prolyl residue of the catalyst and α-chiral aldehydes. Water soluble prolinamido-glycoside catalysts are easily separable from reaction mixture and can be recycled and re-used several times.展开更多
An efficient synthesis of Biginelli-type compounds using potassium phthalimide as a green, mild, and commercially available organocatalyst in a one-pot, multi-component cyclocondensation reaction of cyclopentanone, al...An efficient synthesis of Biginelli-type compounds using potassium phthalimide as a green, mild, and commercially available organocatalyst in a one-pot, multi-component cyclocondensation reaction of cyclopentanone, aldehydes, and urea/thiourea is reported. The present methodology is a green approach to access 4-aryl-7-(aryImethylene)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-ones/thiones. It offers several merits such as simple operational procedures, no use of hazardous organic solvents, and cheap and environmentally friendly solid basic catalyst.展开更多
An efficient asymmetric domino reaction of amino aldehyde to β,γ-unsaturated a-keto esters was achieved by using trans-perhydroindolic acid ld as a chiral organocatalyst with excellent asymmetric behavior. Under the...An efficient asymmetric domino reaction of amino aldehyde to β,γ-unsaturated a-keto esters was achieved by using trans-perhydroindolic acid ld as a chiral organocatalyst with excellent asymmetric behavior. Under the opti- mal reaction conditions, products with more than 99% de and up to 93% ee were obtained in high chemical yield (up to 98%) for a series of β,γ-unsaturated a-keto esters. The methodology provided an efficient route to dihydro- pyran derivatives containing many substituent groups (including amino groups).展开更多
1 Results Much effort has been focused on organocatalytic asymmetric synthesis in these several years. We have already documented highly efficient organocatalytic asymmetric acylation of a wide variety of racemic alco...1 Results Much effort has been focused on organocatalytic asymmetric synthesis in these several years. We have already documented highly efficient organocatalytic asymmetric acylation of a wide variety of racemic alcohols and meso-diols catalyzed bya chiral 1,2-diamine derived from (S)-proline[1]. (S)-Homoproline seems to be a potentially interesting organocatalyst, but no examples using (S)-homoproline itself in asymmetric synthesis has been reported. We have accomplished an efficient and practical syn...展开更多
Imidazol-1-yl-acetic acid is introduced as a new, efficient and recyclable green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst is water solub...Imidazol-1-yl-acetic acid is introduced as a new, efficient and recyclable green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst is water soluble and can be separated from the products by simple filtration. The filtrate can be evaporated to dryness and recrystallized from cool methanol to give the recovered catalyst. This organocatalyst was used for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-flee conditions and recycled up to 8 consecutive runs without any losing of its efficiency.展开更多
A convenient method for Morita-Baylis-Hillman reaction of arylaldehydes with methyl acrylate has been developed by using fluorous-tag organocatalyst 1-[4-(perfluorooctyl)phenyl]-3-phenylthiourea and DABCO at room te...A convenient method for Morita-Baylis-Hillman reaction of arylaldehydes with methyl acrylate has been developed by using fluorous-tag organocatalyst 1-[4-(perfluorooctyl)phenyl]-3-phenylthiourea and DABCO at room temperature. The fluorous organocatalyst could be recovered from the reaction mixture by fluorous solid-phase extraction (F-SPE) with excellent purity for direct reuse.展开更多
Homogeneous gold catalysis has demonstrated the preponderant capability of realizing a broad range of synthetically versatile alkyne functionalization over the last two decades.Though catalytic asymmetric alkyne trans...Homogeneous gold catalysis has demonstrated the preponderant capability of realizing a broad range of synthetically versatile alkyne functionalization over the last two decades.Though catalytic asymmetric alkyne transformation has focused on the principle of using gold catalysts either associated with chiral phosphine ligand or combined with chiral counterion,a variety of breakthroughs have been reported with the application of gold-complex and chiral organocatalyst cooperative catalysis strategy,which could enable the challenging transformations that cannot be realized by mono-catalysis with excellent stereoselectivity.This review will cover two general protocols in this field,including relay catalysis and synergistic catalysis,with emphasis on the detailed cooperative catalysts models to illustrate the roles of the two catalysts and highlight the potential synthetic opportunities offered by asymmetric cooperative catalysis.展开更多
A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the op...A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the optimal conditions, the reactions occurred with moderate-to-excellent enantioselectivities (up to 98% ee). A plausible transition state constructed by the supra- molecular interaction of hydrogen bond and cation-π between catalysts and substrates has been proposed.展开更多
In the recent decade, the development and application of organocatalysis for CO_2 transformation into useful chemicals have attracted much attention. Among these organocatalysts, Lewis base-CO_2 adducts(LB-CO_2) were ...In the recent decade, the development and application of organocatalysis for CO_2 transformation into useful chemicals have attracted much attention. Among these organocatalysts, Lewis base-CO_2 adducts(LB-CO_2) were found to be more efficient.The used Lewis base has great effect on the catalytic activity of its CO_2 adduct. This review reports the recent progress in LB-CO_2 adducts catalyzed the cyclization of CO_2 with epoxides or aziridines to afford cyclic carbonates or oxazolidinones,the carboxylation of CO_2 with propargylic alcohols to α-alkylidene cyclic carbonates, and the reduction of CO_2 to methanol,formamides and methylamines, with the focus on the catalytic mechanism.展开更多
Easily accessible (1R,2S)-1,2-diphenyl-2-formamidoethanol has been developed as an effective Lewis base catalyst in the enantioselective hydrosilylation of ketimines, affording high isolated yields (up to 94%) and mod...Easily accessible (1R,2S)-1,2-diphenyl-2-formamidoethanol has been developed as an effective Lewis base catalyst in the enantioselective hydrosilylation of ketimines, affording high isolated yields (up to 94%) and moderate to high enantioselectivities (up to 82% ee) for a broad range of ketimines.展开更多
文摘Herein we report an efficient organocatalyst for the multicomponent Hantzsch reaction under mild condition.The product easily isolated by simple filtration and catalyst can be recovered.
文摘Six compounds including five proline derivatives have been prepared and tested as chiral organocatalysts for enantioselective aldol reactions and Michael additions. The enantiomeric excesses, which are highly dependent on the molecular structure of catalysts as well as experimental conditions, have reached over 98%.
文摘The backbone of D-glucosamine hydrochloride was fine-tuned and modified by protecting the hydroxyl groups. In order to reduce imines with trichlorosilane, the carbohydrate-derived organocatalysts were prepared and screened. Methyl-4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyr anoside was found as the best catalyst. The reduction was proceeded under CHCl3 as solvent at 40?C, affording 68% - 94% yield.
文摘Prolinamido-glycoside catalyzed asymmetric aldol reaction in aqueous media is reported. The reactions are rapid and highly stereoselective when water is used as solvent. The stereoselectivities were under influence of configurations of a prolyl residue of the catalyst and α-chiral aldehydes. Water soluble prolinamido-glycoside catalysts are easily separable from reaction mixture and can be recycled and re-used several times.
基金Damghan University Research Council for partial support
文摘An efficient synthesis of Biginelli-type compounds using potassium phthalimide as a green, mild, and commercially available organocatalyst in a one-pot, multi-component cyclocondensation reaction of cyclopentanone, aldehydes, and urea/thiourea is reported. The present methodology is a green approach to access 4-aryl-7-(aryImethylene)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2(5H)-ones/thiones. It offers several merits such as simple operational procedures, no use of hazardous organic solvents, and cheap and environmentally friendly solid basic catalyst.
文摘An efficient asymmetric domino reaction of amino aldehyde to β,γ-unsaturated a-keto esters was achieved by using trans-perhydroindolic acid ld as a chiral organocatalyst with excellent asymmetric behavior. Under the opti- mal reaction conditions, products with more than 99% de and up to 93% ee were obtained in high chemical yield (up to 98%) for a series of β,γ-unsaturated a-keto esters. The methodology provided an efficient route to dihydro- pyran derivatives containing many substituent groups (including amino groups).
文摘1 Results Much effort has been focused on organocatalytic asymmetric synthesis in these several years. We have already documented highly efficient organocatalytic asymmetric acylation of a wide variety of racemic alcohols and meso-diols catalyzed bya chiral 1,2-diamine derived from (S)-proline[1]. (S)-Homoproline seems to be a potentially interesting organocatalyst, but no examples using (S)-homoproline itself in asymmetric synthesis has been reported. We have accomplished an efficient and practical syn...
基金the Islamic Azad University,Sousangerd Branch and Yasouj University for the financial support
文摘Imidazol-1-yl-acetic acid is introduced as a new, efficient and recyclable green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst is water soluble and can be separated from the products by simple filtration. The filtrate can be evaporated to dryness and recrystallized from cool methanol to give the recovered catalyst. This organocatalyst was used for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-flee conditions and recycled up to 8 consecutive runs without any losing of its efficiency.
基金the project of"Excellence Initiative"and"Zijin Star"in NJUST,"Doctoral Fund of Ministry of Education of China"(No.200802881024)"National Natural Science Foundation of China"(No.20902047) for financial support
文摘A convenient method for Morita-Baylis-Hillman reaction of arylaldehydes with methyl acrylate has been developed by using fluorous-tag organocatalyst 1-[4-(perfluorooctyl)phenyl]-3-phenylthiourea and DABCO at room temperature. The fluorous organocatalyst could be recovered from the reaction mixture by fluorous solid-phase extraction (F-SPE) with excellent purity for direct reuse.
基金Support for this research from the National Natural Science Foundation of China (Nos. 21971262, 81702255)National Postdoctoral Program for Innovative Talents (No. BX20190399)+1 种基金Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery (No. 2019B030301005)The Program for Guangdong Introducing Innovative and Entrepreneurial Teams (No. 2016ZT06Y337)
文摘Homogeneous gold catalysis has demonstrated the preponderant capability of realizing a broad range of synthetically versatile alkyne functionalization over the last two decades.Though catalytic asymmetric alkyne transformation has focused on the principle of using gold catalysts either associated with chiral phosphine ligand or combined with chiral counterion,a variety of breakthroughs have been reported with the application of gold-complex and chiral organocatalyst cooperative catalysis strategy,which could enable the challenging transformations that cannot be realized by mono-catalysis with excellent stereoselectivity.This review will cover two general protocols in this field,including relay catalysis and synergistic catalysis,with emphasis on the detailed cooperative catalysts models to illustrate the roles of the two catalysts and highlight the potential synthetic opportunities offered by asymmetric cooperative catalysis.
基金financial support from the National Natural Science Foundation of China (21002009, 21072093 & 20872051)the Doctoral Fund of Ministry of Education of China (20090091110017)+1 种基金Priority Academic Program Development of Jiangsu Higher Education Institutionsalso supported by the Fundamental Research Funds for the Central Universities (1107020526 & 1103020505)
文摘A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the optimal conditions, the reactions occurred with moderate-to-excellent enantioselectivities (up to 98% ee). A plausible transition state constructed by the supra- molecular interaction of hydrogen bond and cation-π between catalysts and substrates has been proposed.
基金supported by the National Natural Science Foundation of China(21402021)the Program for Changjiang Scholars and Innovative Research Team in University(IRT13008)
文摘In the recent decade, the development and application of organocatalysis for CO_2 transformation into useful chemicals have attracted much attention. Among these organocatalysts, Lewis base-CO_2 adducts(LB-CO_2) were found to be more efficient.The used Lewis base has great effect on the catalytic activity of its CO_2 adduct. This review reports the recent progress in LB-CO_2 adducts catalyzed the cyclization of CO_2 with epoxides or aziridines to afford cyclic carbonates or oxazolidinones,the carboxylation of CO_2 with propargylic alcohols to α-alkylidene cyclic carbonates, and the reduction of CO_2 to methanol,formamides and methylamines, with the focus on the catalytic mechanism.
基金supported by the National Natural Science Foundation of China (20672107 and 20732006)
文摘Easily accessible (1R,2S)-1,2-diphenyl-2-formamidoethanol has been developed as an effective Lewis base catalyst in the enantioselective hydrosilylation of ketimines, affording high isolated yields (up to 94%) and moderate to high enantioselectivities (up to 82% ee) for a broad range of ketimines.