Wengang Guo

Wengang Guo
Chinese Academy of Sciences | CAS · State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics

PhD
Changzhou University, Lab site: www.x-mol.com/groups/wgguo

About

32
Publications
1,949
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605
Citations
Citations since 2016
23 Research Items
575 Citations
2016201720182019202020212022020406080
2016201720182019202020212022020406080
2016201720182019202020212022020406080
2016201720182019202020212022020406080

Publications

Publications (32)
Article
Full-text available
Disclosed here is a catalytic asymmetric azidation reaction for the efficient synthesis of α-azido ketones bearing a labile tertiary stereocenter. With a superb chiral squaramide catalyst, a mild asymmetric formal H-N3 insertion of α-carbonyl sulfoxonium ylides proceeded with excellent efficiency and enantioselectivity. This organocatalytic process...
Article
A new organocatalytic asymmetric method for the synthesis of enantioenriched triarylmethanes is developed. Different from the conventional approaches featuring asymmetric arylation, the present study employs asymmetric reduction via C-H bond formation as the key step. This approach does not require the presence of a heteroaryl ring or the presynthe...
Article
We have developed a catalytic asymmetric allylic substitution/isomerization process with central chirality transposition. This process takes advantage of the ambident reactivity of the 2-indole imine methide generated in situ from racemic tertiary indolylmethanols. The use of a suitable chiral phosphoric acid catalyst and an ortho-directing group a...
Article
Full-text available
While asymmetric insertion of metal carbenes into H−X (X = C, N, O, etc.) bond has been well-established, asymmetric control over free carbenes is challenging due to the presence of...
Article
A new intermolecular approach for the expedient access to cyclopropane-incorporated tricyclic skeleton from the readily available isobenzopyryliums and vinyl boronic acids has been achieved. This protocol does not involve the highly active carbenoid intermediates or strong conditions as compared to traditional approaches. Abstract Cyclopropanes em...
Article
Cyclopropanes embedded in a polycyclic bridged architecture are a versatile structural motif, but such complex frameworks often impose substantial synthetic challenges. Herein we introduce a new approach for the expedient access to such spring‐loaded strained systems via an exceptionally mild intermolecular convergent process between the readily av...
Article
Full-text available
Described here is the first organocatalytic asymmetric N−H insertion reaction of α-carbonyl sulfoxonium ylides. Without a metal catalyst, this reaction represents an attractive complement to the well-established carbene insertion reactions. As a stable surrogate of diazocarbonyl compounds, sulfoxonium ylides reacted with a range of aryl amines to p...
Article
Full-text available
Herein we disclose a new catalytic asymmetric approach for the synthesis of chiral α-amino ketones, which is particularly useful for the less accessible acyclic α-tertiary cases. By a protonation-amination sequence, our approach represents a rare asymmetric H−heteroatom bond insertion by α-carbonyl sulfonium ylides, an attractive surrogate of diazo...
Article
An unusual skeletal reorganization of oxetanes is described, in which oxetane‐tethered anilines reacted unexpectedly to form 1,2‐dihydroquinolines in the presence of In(OTf)3 as catalyst. This process proceeds through an intriguing mechanism involving a series of bond cleavage and formation steps. Abstract Skeletal reorganization is a type of fasc...
Article
Skeletal reorganization is a type of fascinating transformations owing to their intriguing mechanisms and utility in complex molecule synthesis. However, these reactions are limitedly known for most functional groups. Herein, we describe such an unusual process of oxetanes. In the presence of In(OTf)3 as catalyst, oxetane‐tethered anilines reacted...
Article
A water promoted asymmetric aldol/lactonization/enolization cascade reaction of α-keto acids and α-keto esters was developed, affording the first general protocol for the construction of chiral quaternary isotetronic acids with excellent enantioselectivity. Theoretical results indicate that intramolecular ionized enamine intermediates stabilized by...
Article
Full-text available
Chiral tetrahydrothiophenes and tetrahydroselenophenes are highly useful structural units. Here we describe a new catalytic asymmetric approach for their synthesis. With a suitable chiral Brønsted acid catalyst, an oxetane desymmetrization by a well‐positioned internal sulfur or selenium nucleophile proceeded efficiently to generate all‐carbon quat...
Article
Chiral tetrahydrothiophenes and tetrahydroselenophenes are highly useful structural units. Here we describe a new catalytic asymmetric approach for their synthesis. With a suitable chiral Brønsted acid catalyst, an oxetane desymmetrization by a well‐positioned internal sulfur or selenium nucleophile proceeded efficiently to generate all‐carbon quat...
Article
Full-text available
Correction for ‘An organic-base catalyzed asymmetric 1,4-addition of tritylthiol to in situ generated aza- o -quinone methides at the H 2 O/DCM interface’ by Xianghui Liu et al. , Chem. Commun. , 2019, 55 , 2668–2671.
Article
Based on an efficient method for in situ generation of N-o-QMs species in the presence of base, enantioselective catalytic conjugated additions of tritylthiol to in situ generated N-o-QMs are reported....
Article
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Chiral spirooxindole is the core structure of a large number of natural and unnatural products with biological activities. However, the construction of trispirocyclic oxindoles remains challenging due to the difficulty in the assembly such complex skeleton and control the stereoselectivities of the multiple quaternary stereocenters. Herein, we pres...
Article
Full-text available
The unique physicochemical properties of water as solvent have attracted the great interest of synthetic chemists for many years and tremendous research progress on chemical reactions under aqueous conditions has been reported. Among them, catalytic asymmetric reactions have also been demonstrated and water turns out to not only be a unique solvent...
Article
We report herein a dynamic kinetic resolution (DKR) involving ortho-quinone methide (o-QM) intermediates. In the presence of Et3 N and the cinchonine-derived nucleophilic catalyst D, the DKR of 2-sulfonylalkyl phenols with allenic esters afforded chiral benzylic sulfones in 57-79 % yield with good to excellent enantioselectivity (85-95 % ee). Furth...
Article
Full-text available
The first enantioselective catalytic 1,2-hydroperoxidation has been achieved in the presence of PEG-600 using an acid−base bifunctional chiral squaramide as the organocatalyst, affording a range of enantioenriched α-N-substituted hydroperoxides bearing an oxindole moiety with excellent stereoselectivities (up to 99% ee).
Article
We report herein a dynamic kinetic resolution (DKR) involving ortho-quinone methide (o-QM) intermediates. In the presence of Et3N and the cinchonine-derived nucleophilic catalyst D, the DKR of 2-sulfonylalkyl phenols with allenic esters afforded chiral benzylic sulfones in 57–79 % yield with good to excellent enantioselectivity (85–95 % ee). Furthe...
Article
Full-text available
4-Thiazolidinone is regarded as a privileged structural unit in bioactive compounds. However, there is still no example of a catalytic method for the synthesis of chiral 4-thiazolidinone until now. We reported herein a facile and efficient method for the construction of chiral spirooxindole-based 4-thiazolidinone. This methodology is based on the a...
Article
A highly enantioselective approach for the synthesis of 3-alkyl- indole or indoline derivatives with a functional thiol group is presented. The chemistry is based on the asymmetric 1,4-addition of thiol to vinylogous imine intermediates, which are generated in situ from sulfonylindoles. The broad substrate transformation proceeds with high yields (...
Article
Full-text available
The enantioselective conjugated addition of tritylthiol to in situ generated ortho-quinone methides (o-QMs) is catalyzed by an acid-base bifunctional squaramide organocatalyst. The transformation proceeds with high yield (up to 99 %) and stereoselectivity (up to 97:3 e.r.) using water as solvent under mild conditions. The catalyst system provides a...
Article
Full-text available
The enantioselective conjugated addition of tritylthiol to in situ generated ortho-quinone methides (o-QMs) is catalyzed by an acid–base bifunctional squaramide organocatalyst. The transformation proceeds with high yield (up to 99 %) and stereoselectivity (up to 97:3 e.r.) using water as solvent under mild conditions. The catalyst system provides a...
Article
Full-text available
A series of of amphiphilic imidazole based secondary and primary amine catalysts were synthesized and shown to be very effective with an acid cocatalyst for the asymmetric reaction of cyclohexanone to β,γ-unsaturated α-keto ester. Interestingly, primary and secondary amine catalysts show different regio-selectivities in this reaction. Under the cat...
Article
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For the first time a direct asymmetric aldol reaction of free hydroxyacetone and activated ketones is achieved by using the new title catalyst.
Article
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Unprecedented organocatalyzed asymmetric cascade reactions have been developed for the facile synthesis of chiral spirooxindole-based isotetronic acids and 5-1H-pyrrol-2-ones.The asymmetric 1,2-addition reactions of α-ketoesters to isatins and imines by using an acid–base bifunctional 6′-OH cinchona alkaloid catalyst, followed by cyclization and en...
Article
Full-text available
Michael addition was catalyzed by a new amphiphilic proline]derived mercapto imidazole organic catalyst using water as solvent with high diastereoselectivity (99:1 d.r.) and execellent enantioselectivity (96% ee).

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