Dong Xing

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Name: 刑栋; Xing, Dong

Organization: East China Normal University , China

Department: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development

Title: (PhD)

TOPICS

Organic Chemistry

Chemicals
References

Catalyst-Free Halogenation of α-Diazocarbonyl Compounds with N-Halosuccinimides: Synthesis of 3-Halooxindoles or Vinyl Halides

Co-reporter:Chaoqun Ma, Dong Xing, and Wenhao Hu

Organic Letters 2016 Volume 18(Issue 13) pp:3134-3137

Publication Date(Web):June 16, 2016

DOI:10.1021/acs.orglett.6b01346

A novel catalyst-free halogenative cyclization of N-aryl diazoamides with N-halosuccinimides (NXS) is reported for the synthesis of 3-halooxindoles through a carbene-free mechanism. N-Aryl diazoamides reacted with NXS under mild and catalyst-free conditions to afford the corresponding 3-halooxindoles in good yields. This transformation is proposed to proceed through diazonium ion formation followed by intramolecular Friedel–Crafts alkylation.

Enantioselective Synthesis of α-Mercapto-β-amino Esters via Rh(II)/Chiral Phosphoric Acid-Cocatalyzed Three-Component Reaction of Diazo Compounds, Thiols, and Imines

Co-reporter:Guolan Xiao, Chaoqun Ma, Dong Xing, and Wenhao Hu

Organic Letters 2016 Volume 18(Issue 23) pp:6086-6089

Publication Date(Web):November 22, 2016

DOI:10.1021/acs.orglett.6b03075

An enantioselective method for the synthesis of α-mercapto-β-amino esters has been developed via a rhodium(II)/chiral phosphoric acid-cocatalyzed three-component reaction of diazo compounds, thiols, and imines. This transformation is proposed to proceed through enantioselective trapping of the sulfonium ylide intermediate generated in situ from the diazo compound and thiol by the phosphoric acid-activated imine. With this method, a series of α-mercapto-β-amino esters were obtained in good yields with moderate to good stereoselectivities.

Divergent synthesis of chiral heterocycles via sequencing of enantioselective three-component reactions and one-pot subsequent cyclization reactions

Co-reporter:Min Tang, Dong Xing, Haoxi Huang and Wenhao Hu

Chemical Communications 2015 vol. 51(Issue 53) pp:10612-10615

Publication Date(Web):01 Apr 2015

DOI:10.1039/C5CC01979F

A highly efficient sequencing of catalytic asymmetric three-component reactions of alcohols, diazo compounds and aldimines/aldehydes with one-pot subsequent cyclization reactions was reported. The development of a robust and versatile Rh(II)/Zr(IV)–BINOL co-catalytic system not only gives high diastereo- and enantioselective controls of the three-component reaction, but also shows excellent functionality tolerances that allow a wide range of functionalities to be pre-installed in each component and readily undergo one-pot subsequent cyclization reactions, thus providing rapid and diversity-oriented synthesis (DOS) of different types of chiral nitrogen- and/or oxygen-containing polyfunctional heterocycles.

Catalytic Asymmetric Four-Component Reaction for the Rapid Construction of 3,3-Disubstituted 3-Indol-3′-yloxindoles

Co-reporter:Changcheng Jing, Dong Xing, and Wenhao Hu

Organic Letters 2015 Volume 17(Issue 17) pp:4336-4339

Publication Date(Web):August 25, 2015

DOI:10.1021/acs.orglett.5b02160

A Rh(II)/chiral phosphoric acid cocatalyzed four-component reaction of indoles, 3-diazooxindoles, arylamines, and ethyl glyoxylate is developed, offering an extremely efficient strategy for the construction of 3,3-disubstituted 3-indol-3′-yloxindoles with excellent diastereoselectivities and high to excellent enantioselectivities. This transformation is proposed to proceed through a Mannich-type trapping of the zwitterionic intermediate generated from a metal carbene and an indole with an iminoester derived from an arylamine and a glyoxylate.

Divergent Synthesis of Multisubstituted Tetrahydrofurans and Pyrrolidines via Intramolecular Aldol-type Trapping of Onium Ylide Intermediates

Co-reporter:Changcheng Jing;Dr. Dong Xing;Lixin Gao;Dr. Jia Li;Dr. Wenhao Hu

Chemistry - A European Journal 2015 Volume 21( Issue 52) pp:19202-19207

Publication Date(Web):

DOI:10.1002/chem.201503621

Abstract

This paper reports a divergent strategy for the synthesis of multisubstituted tetrahydrofurans and pyrrolidines, starting from easily accessible β-hydroxyketones or β-aminoketones to react with diazo compounds. Under Rh^II catalysis, this transformation is proposed to proceed through a metal–carbene-induced oxonium ylide or ammonium ylide formation followed by an intramolecular aldol-type trapping of these active intermediates. A series of highly substituted tetrahydrofurans and pyrrolidines are synthesized in high yields with good to excellent diastereoselectivities. Preliminary biological evaluations revealed that both types of heterocycles show good PTP1B inhibitory activities.

Synthesis of 3-(hydroxymethyl)-3-indol-3′-yloxindoles via Rh(II)-catalyzed three-component reaction of 3-diazooxindoles, indoles and formalin

Co-reporter:Changcheng Jing, Dong Xing, Chengjin Wang, Wenhao Hu

Tetrahedron 2015 Volume 71(Issue 22) pp:3597-3602

Publication Date(Web):3 June 2015

DOI:10.1016/j.tet.2015.02.053

An efficient rhodium(II)-catalyzed three-component reaction of 3-diazooxindoles, indoles and formalin was reported. With this transformation, a series of 3-(hydroxymethyl)-3-indol-3′-yloxindoles were easily afforded in good to excellent yields. The resulted 3-(hydroxymethyl)-3-indol-3′-yloxindole could be easily converted to the key intermediate for the total synthesis of gliocladin C.

Facile Synthesis of 3-Aryloxindoles via Brønsted Acid Catalyzed Friedel–Crafts Alkylation of Electron-Rich Arenes with 3-Diazooxindoles

Co-reporter:Changwei Zhai, Dong Xing, Changcheng Jing, Jun Zhou, Chengjin Wang, Dongwei Wang, and Wenhao Hu

Organic Letters 2014 Volume 16(Issue 11) pp:2934-2937

Publication Date(Web):May 15, 2014

DOI:10.1021/ol5010752

A simple metal-free method for the synthesis of 3-aryloxindoles via Brønsted acid catalyzed aromatic C–H functionalization of electron-rich arenes with 3-diazooxindoles is developed. In the presence of a catalytic amount of TfOH, a series of 3-aryloxindoles are synthesized as single regioisomers in good to excellent yields. This transformation is proposed to proceed through acid-catalyzed protonation of 3-diazooxindoles into diazonium ions followed by Friedel–Crafts-type alkylation of arenes.

Inside Cover: Catalytic Asymmetric Functionalization of Aromatic CH Bonds by Electrophilic Trapping of Metal-Carbene-Induced Zwitterionic Intermediates (Angew. Chem. Int. Ed. 48/2014)

Co-reporter:Shikun Jia;Dr. Dong Xing;Dan Zhang ;Dr. Wenhao Hu

Angewandte Chemie International Edition 2014 Volume 53( Issue 48) pp:

Publication Date(Web):

DOI:10.1002/anie.201409113

Catalytic Asymmetric Functionalization of Aromatic CH Bonds by Electrophilic Trapping of Metal-Carbene-Induced Zwitterionic Intermediates

Co-reporter:Shikun Jia;Dr. Dong Xing;Dan Zhang ;Dr. Wenhao Hu

Angewandte Chemie International Edition 2014 Volume 53( Issue 48) pp:13098-13101

Publication Date(Web):

DOI:10.1002/anie.201406492

Abstract

Asymmetric functionalization of aromatic CH bonds of N,N-disubstituted anilines with diazo compounds and imines is reported for the efficient construction of α,α-diaryl benzylic quaternary stereocenters in good yields with high diastereoselectivities and excellent enantioselectivities. This Rh^II/chiral phosphoric acid cocatalyzed transformation is proposed to proceed through a metal-carbene-induced zwitterionic intermediate which undergoes electrophilic trapping. To the best of our knowledge, this is the first asymmetric example of metal carbene-induced intermolecular functionalization of aryl CH bonds.

Synthesis of 3-Amino-3-hydroxymethyloxindoles and 3-Hydroxy-3-hydroxymethyloxindoles by Rh2(OAc)4-Catalyzed Three-Component Reactions of 3-Diazooxindoles with Formaldehyde and Anilines or Water

Co-reporter:Chengjin Wang, Dong Xing, Dongwei Wang, Xiang Wu, and Wenhao Hu

The Journal of Organic Chemistry 2014 Volume 79(Issue 9) pp:3908-3916

Publication Date(Web):April 4, 2014

DOI:10.1021/jo500307n

Efficient Rh(II)-catalyzed three-component reactions of 3-diazooxindoles and formaldehyde with either anilines or water were developed to give a series of substituted 3-amino-3-hydroxymethyloxindoles or 3-hydroxy-3-hydroxymethyloxindoles in good to excellent yields. In this atom- and step-economic transformation, Rh2(OAc)4-catalyzed decomposition of 3-diazooxindoles with anilines or water forms the corresponding active ammonium or oxonium ylides. Electrophilic trapping of the resulting ammonium ylides or oxonium ylides by formaldehyde in the form of formalin efficiently produces the title compounds in one step.

Catalytic Asymmetric Functionalization of Aromatic CH Bonds by Electrophilic Trapping of Metal-Carbene-Induced Zwitterionic Intermediates

Co-reporter:Shikun Jia;Dr. Dong Xing;Dan Zhang ;Dr. Wenhao Hu

Angewandte Chemie 2014 Volume 126( Issue 48) pp:13314-13317

Publication Date(Web):

DOI:10.1002/ange.201406492

Abstract

Innentitelbild: Catalytic Asymmetric Functionalization of Aromatic CH Bonds by Electrophilic Trapping of Metal-Carbene-Induced Zwitterionic Intermediates (Angew. Chem. 48/2014)

Co-reporter:Shikun Jia;Dr. Dong Xing;Dan Zhang ;Dr. Wenhao Hu

Angewandte Chemie 2014 Volume 126( Issue 48) pp:

Publication Date(Web):

DOI:10.1002/ange.201409113

Iron Porphyrin-Catalyzed Three-Component Reaction of Ethyl Diazoacetate with Aliphatic Amines and β,γ-Unsaturated α-Keto Esters

Co-reporter:Chaoqun Ma, Dong Xing, Changwei Zhai, Jiuwei Che, Shunying Liu, Jue Wang, and Wenhao Hu

Organic Letters 2013 Volume 15(Issue 24) pp:6140-6143

Publication Date(Web):November 19, 2013

DOI:10.1021/ol403011r

An iron porphyrin-catalyzed three-component reaction of ethyl diazoacetate with aliphatic amines and β,γ-unsaturated α-keto esters is reported. The use of iron porphyrin catalyst allows aliphatic amines to be used as the substrate without encountering catalyst poisoning issue and a series of β-hydroxy-α-amino esters are produced in high yields with excellent regioselectivities.

Highly Efficient Synthesis of Mixed 3,3′-Bisindoles via Rh(II)-Catalyzed Three-Component Reaction of 3-Diazooxindoles with Indoles and Ethyl Glyoxylate

Co-reporter:Dong Xing, Changcheng Jing, Xinfeng Li, Huang Qiu, and Wenhao Hu

Organic Letters 2013 Volume 15(Issue 14) pp:3578-3581

Publication Date(Web):June 28, 2013

DOI:10.1021/ol401414w

A series of mixed 3,3′-bisindoles were efficiently synthesized via a Rh2(OAc)4-catalyzed three-component reaction of 3-diazooxindoles with indoles and ethyl glyoxylate in high yields with excellent diastereoselectivities. The product easily underwent further synthetic transformations and could be potentially applied to the total synthesis of (±)-gliocladin C and related natural alkaloids.

Divergent synthesis of chiral heterocycles via sequencing of enantioselective three-component reactions and one-pot subsequent cyclization reactions

Co-reporter:Min Tang, Dong Xing, Haoxi Huang and Wenhao Hu

Chemical Communications 2015 - vol. 51(Issue 53) pp:NaN10615-10615

Publication Date(Web):2015/04/01

DOI:10.1039/C5CC01979F