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Robin
Chi Research Group OrganoCatalysis, Chemical Synthesis,
Functional Molecules
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The Chi laboratory is committed to the state-of-art
original chemistry research that addresses problems of both fundamental and
practical significance. A key objective is to develop green and efficient
synthetic methods to make functional molecules, and to understand the
principles guiding the bong breaking and formation events. We focus on the
development of fundamentally novel basic catalytic activation modes with
useful synthetic applications for the preparation of pharmaceuticals,
agriculture chemicals, fine chemicals, and for efficient assembly and/or
modification of polymers, biomolecules, and other functional molecules. Over
the past years, we have developed new activation modes and synthetic
transformations enabled by N-Heterocyclic Carbene (NHC) as the key organic
catalyst. Immediate applications of my lab’s new catalytic approaches
include concise and green processes for bioactive molecules such as valuable
non-natural amino acids and their derivatives. On the fundamental side, our
research has created new understanding of chemical reactivities and new
concept on catalytic activations. The lab has also taken serous efforts on
collaborative development on bioactive molecules and functional materials,
and applied research for innovation and entrepreneurship. Examples of the lab’s
research include: § NHC
organic catalyst-enabled activation of carboxylic esters, including
activation of the inert beta-sp3-carbon of saturated esters. § Biomimetic
single-electron-transfer (SET) radical reactions enabled by NHC catalysts. § Oxidative
NHC catalysis and reaction controls of aldehydes, including remote-carbon
functionalization. § Cooperative
catalysis merging NHCs with other catalysts (such as transition metal
catalysts, Lewis acid catalysts, and other organic catalysts). § Rapid
synthesis functional molecules via new NHC catalysis, including ongoing
studies for concise asymmetric total synthesis of complex natural products. § Multi-disciplinary
collaborative research, and application-driven research for innovation and entrepreneurship |
Robin Chi Full
Professor; NRF Investigator Education:
Undergraduate:
Tsinghua & HKBU (2002) PhD:
UW-Madison, USA (under Sam Gellman, 2007) Postdoc:
UC-Berkeley USA (under Jean Fréchet, 2009) Recent
Recognitions: 2017
Chemical Society of Japan (CSJ) Lectureship 2016
Aldrich-Yale Lectureship 2016
Nanyang Research Award (Young Investigator) 2015
NRF Investigatorship Award 2013
Singapore Young Scientist Award 2012
Thieme Chemistry Journal Award 2012
NTU SPMS Teaching Excellence Award 2011,
2012, 2013 ACP Lectureship Awards 2010
GSK-EDB Award on Manufacturing 2009
Singapore NRF Fellowship Contact: robinchi@ntu.edu.sg 21 Nanyang Link, SPMS-CBC 06-19,
NTU, Singapore 637371 Administrative Assistant/Lab Manager: Dr. Lin Hao SPMS-CBC-06-41 |
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The Chi group welcomes self-motivated, creative, and hard-working individuals in the
following areas: § Priorities will be given to Singaporeans and
Singapore Permanent Residents § Synthetic Chemistry (particularly with experience
in Natural Product synthesis), Electrochemistry; Polymer Materials; Physical
Organic Chemistry (with Mechanistic Studies). § Individuals with Industrial Experience, Scale up
and Process Development § Self-Financed Researchers and Students (Highly
Motivated and Hard-Working) § Exceptional Individuals in other
areas will also be considered. |
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2019 |
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"Catalytic
asymmetric acetalization of carboxylic acids for access to chiral phthalidyl
ester prodrugs" |
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"Enantiomeric
glycosylated cationic block co-beta-peptides eradicate Staphylococcus aureus biofilms
and antibiotic-tolerant persisters" |
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109. Jun Xu, Lixin
Liang, Haohao Zheng, Yonggui Robin Chi, and Rongbiao Tong* "Green
oxidation of indoles using halide catalysis" |
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"Carbene-Catalyzed
Dynamic Kinetic Resolution and Asymmetric Acylation of Hydroxyphthalides and
Related Natural Products" Angew. Chem. Int. Ed.
2019. DOI:10.1002/anie.201910922 (PDF), (online) |
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"Carbene-Catalyzed
Desymmetrization and Direct Construction of Arenes with All-Carbon Quaternary
Chiral Center" Angew. Chem.
Int. Ed. 2019, 58, 15778-15782, (PDF), (online) |
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"Access
to Cyclic β‐Amino Acids by Amine‐Catalyzed
Enantioselective Addition of the γ‐Carbon Atoms of α,β‐Unsaturated
Imines to Enals"
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"Gold and Carbene
Relay Catalytic Enantioselective Cycloisomerization/Cyclization Reactions of
Ynamides and Enals" Angew. Chem.
Int. Ed. 2019, DOI:10.1002/anie.201910922, (PDF), (online) |
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"Access
to All-Carbon Spirocycles through a Carbene and Thiourea Cocatalytic
Desymmetrization Cascade Reaction" |
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"Sulfinate
and Carbene Co-catalyzed Rauhut-Currier Reaction for Enantioselective Access
to Azepino[1,2-a]indole" |
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102. Jianrong Steve Zhou*, Shenghan Teng, Zhiwei
Jiao, and Yonggui Robin Chi "Asymmetric
Wacker‐Type oxyallenylation and Azaallenylation of Cyclic
Alkenes" Angew.
Chem. Int. Ed. 2019, DOI:10.1002/anie.201911961, (PDF), (online) |
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101. Runjiang Song and
Yonggui Robin Chi* "N-Heterocyclic
Carbene Catalyzed Radical Coupling of Aldehydes with Redox-Active
Esters" |
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"Carbene‐Catalyzed
Enantioselective Aromatic N‐Nucleophilic Addition of Heteroarenes
to Ketones" Angew.
Chem. Int. Ed. 2019, DOI:10.1002/anie.201912160, (PDF), (online) |
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"NHC-Catalyzed
Chemoselective Reactions of Enals and Aminobenzaldehydes for Access to Chiral
Dihydroquinolines" Angew. Chem. Int. Ed. 2019, 58, 18410-18413,
(PDF), (online) |
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"Enantioselective
Indole N–H Functionalization Enabled by Addition of Carbene Catalyst to
Indole Aldehyde at Remote Site" |
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"Enantio-
and Diastereoselective Synthesis of Chromeno[4,3-b]pyrrole Derivatives
Bearing Tetrasubstituted Chirality Centers through Carbene Catalyzed Cascade
Reactions" Org. Lett.
2019, DOI: 10.1021/acs.orglett.9b04371 (PDF), (online) |
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"Chiral
Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for
Carbene-Catalyzed Radical Reactions" |
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95. Pengcheng Zheng,
Shuquan Wu, Chengli Mou, Wei Xue, Zhichao Jin, and Yonggui Robin Chi* "Addition of
a Carbene Catalyst to Indole Aryl Aldehyde Activates a Remote δ-sp2 Carbon
for Protonation and Formal [4+2] Reaction" |
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"Carbene-Catalyzed
α‑Carbon Amination of Chloroaldehydes for Enantioselective Access to
Dihydroquinoxaline Derivatives" |
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"NaOH-Promoted
Chemoselective Cascade Cyclization of Cyclopropyl Esters with Unsaturated
Imines: Access to Bioactive Cyclopenta[c]pyridine Derivatives" |
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92. Changyi Liu, Shuquan Wu, Jun Xu, Lingzhu Chen,
Pengcheng Zheng, and Yonggui Robin Chi* "Carbene-Catalyzed
Enantioselective Addition of Thioamides to Bromoenals for Access to
Thiazinone Heterocycles" |
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91. Ye Liu, Yu Shen,
Weina Zhang, Jiena Weng, Meiting Zhao, Tingshun Zhu, Yonggui Robin Chi,
Yanhui Yang, Hua Zhang and Fengwei Huo* "Engineering
channels of metal-organic frameworks to enhance catalytic selectivity" |
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"Carbene‐Catalyzed
Direct Functionalization of the β‐sp3‐Carbon
Atoms of α‐Chloroaldehydes" |
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"Carbene‐Catalyzed
Formal [3 + 3] Cycloaddition Reaction for Access to Substituted 2‐Phenylbenzothiazoles" Eur. J. Org.
Chem.2019, DOI:10.1002/ejoc.201901773, (PDF), (online) |
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88. Jie Ke, Hongling Wang, Liejin Zhou, Chengli
Mou, Jingjie Zhang, Lutai Pan, and Yonggui Robin "Hydrodehalogenation
of Aryl Halides through Direct Electrolysis" |
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87. Pengcheng Zheng,
Chengcheng Li, Moucheng Li, Dingwu Pan, Shuquan Wu, Wei Xue, Zhichao Jin, and
Yonggui Robin Chi* "Efficient
Access to 2-Pyrones via Carbene-Catalyzed Oxidative [3+3] Reactions between
Enals and Nitrogen Ylides" |
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2018 |
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86. Weina Zhang, Bing
Zheng, Wenxiong Shi, Xinyi Chen, Zhiling Xu, Shuzhou Li, Yonggui Robin Chi,
Yanhui Yang, Jun Lu, Wei Huang,
and Fengwei Huo "Site-Selective
Catalysis of a Multifunctional Linear Molecule: The Steric Hindrance of
Metal–Organic Framework Channels" Adv. Mater.
2018, 30, DOI: 10.1002/adma.201800643, (PDF), (online) |
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"Carbene-Catalyzed
Enantioselective Addition of Benzylic Carbon to Unsaturated Acyl Azolium for
Rapid Synthesis of Pyrrolo[3,2-c]quinolines" |
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"Carbene-catalyzed
enantioselective oxidative coupling of enals and di(hetero)arylmethanes" |
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83. Jun Sun, Fangcheng He, Zhongyao Wang, Dingwu Pan, Pengcheng
Zheng, Chengli Mou, Zhichao Jin, and Yonggui Robin Chi* "Carbene-catalyzed
enal γ-carbon addition to α-ketophosphonates for enantioselective access to
bioactive 2-pyranylphosphonates" |
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82. Jun Sun, Chengli
Mou, Zhongyao Wang, Fangcheng He, Jian Wu, and Yonggui Robin Chi* "Carbene-Catalyzed [4 + 2]
Cycloadditions of Vinyl Enolate and (in Situ Generated) Imines for
Enantioselective Synthesis of Quaternary α-Amino Phosphonates" |
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"Kinetic Resolution of 1,2-Diols
via NHC-Catalyzed Site-Selective Esterification" |
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“Addition of N-Heterocyclic Carbene
Catalyst to Aryl Esters Induces Remote C-Si Bond Activation and Benzylic
Carbon Functionalization " |
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"Direct
Activation of β-sp3-Carbons of Saturated Carboxylic Esters as Electrophilic
Carbons via Oxidative Carbene Catalysis" |
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"Enantioselective access to
multi-cyclic α-amino phosphonates via carbene-catalyzed cycloaddition
reactions between enals and six-membered cyclic imines" |
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2017 |
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“A
reaction mode of carbene-catalysed aryl aldehyde activation and induced
phenol OH functionalization" |
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“Polyhalides
as Efficient and Mild Oxidants for Oxidative Carbene Organocatalysis via
Radical Processes” |
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"Construction of Fused Pyrrolidines
and β-Lactones by Carbene-Catalyzed C−N, C−C, and C−O Bond Formations" |
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“Carbene-Catalyzed
Reductive Coupling of Nitrobenzyl Bromide and Nitroalkene via
Singel-Electron-Transfer (SET) process and Formal 1,4-Addition” |
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"Carbene and Acid Cooperative
Catalytic Reactions of Aldehydes and o-Hydroxybenzhydryl Amines for Highly
Enantioselective Access to Dihydrocoumarins" |
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"Carbene-Catalyzed
Formal [5 + 5] Reaction for Coumarin Construction and Total Synthesis of
Defucogilvocarcins" |
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71. Yuhuang
Wang, Xingxing Wu, and Yonggui Robin Chi* "Synthesis of indanes via
carbene-catalyzed single-electron-transfer processes and cascade
reactions" |
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“Sulfoxidation
of alkenes and alkynes with NFSI as a radical initiator and selective
oxidant” |
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"Carbene-catalyzed LUMO
activation of alkyne esters for access to functional pyridines" |
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"Trimerization of enones under air
enabled by NHC/NaOtBu via a SET radical pathway" |
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"Carbene-Catalyzed Indole
3-Methyl C(sp3)–H Bond Functionalization" |
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2016 |
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66.
Zhijian Huang, Xuan Huang, Bao-Sheng Li, Chengli Mou, Song Yang, Bao-An Song,
and Yonggui Robin Chi* "Access
to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed
Desymmetrization of Bisphenols", |
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"Carbene-catalyzed dynamic kinetic resolution
of carboxylic esters", |
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64.
Bao-Sheng Li, Yuhuang Wang, Rupert S. J. Proctor, Yuexia Zhang, Richard D.
Webster, Song Yang, Baoan Song, and Yonggui Robin Chi* "Carbene-catalysed
reductive coupling of nitrobenzyl bromides and activated ketones or imines
via single-electron-transfer process" |
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"Enantioselective Nucleophilic β-Carbon-Atom
Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions", Angew.
Chem. Int. Ed., 2016,
55, 12280-12284, (PDF), (Online) |
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“Polyhalides as Efficient
and Mild Oxidants for Oxidative Carbene Organocatalysis via Radical
Processes” Angew. Chem. Int. Ed. 2016,
in press, DOI:
10.1002/anie.201611692 |
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“Carbene-Catalyzed
Reductive Coupling of Nitrobenzyl Bromide and Nitroalkene via
Singel-Electron-Transfer (SET) process and Formal 1,4-Addition” |
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"Carbene-catalyzed
desymmetrization of 1,3-diols: access to optically enriched tertiary alkyl
chlorides" |
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"Green and Rapid Access to Benzocoumarins via
Direct Benzene Construction through Base-Mediated Formal [4+2] Reaction and
Air Oxidation" |
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"Rapid
access to bicyclic δ-lactones via carbene-catalyzed activation and cascade
reaction of unsaturated carboxylic esters", |
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2015 |
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“N‑Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β‑Hydroxylation of Enals” |
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"N-Heterocyclic Carbene-Catalyzed
δ-Carbon LUMO Activation of Unsaturated Aldehydes", |
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"Carbon-Carbon Bond Activation of
Cyclobutenones Enabled by Addition of Chiral Organocatalyst to Ketone" |
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"Aminomethylation of Enals through
Carbene and Acid Cooperative Catalysis: Concise Access to β2-Amino
Acids" |
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"Cycloaddition
of cyclobutenone and azomethine imine enabled by chiral isothiourea organic
catalysts" |
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"Nucleophilic β-Carbon Activation of
Propionic Acid as a 3-Carbon Synthon by Carbene Organocatalysis" |
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"Oxidative
N-Heterocyclic Carbene-Catalyzed γ-Carbon Addition of Enals to Imines:
Mechanistic Studies and Access to Antimicrobial Compounds" |
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2014 |
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“N-Heterocyclic
Carbene-Catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine
Imines”, |
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"Benzene construction via organocatalytic
formal [3+3] cycloaddition reaction" |
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"Metal
and Carbene Organocatalytic Relay Acitvation of Alkynes for Stereoselective
Reaction" |
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“Access to Oxoquinoline Heterocycles via
N-Heterocyclic Carbene-Catalyzed Ester Activation and Selective Domino
Reaction” |
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46.
Yonggui Robin Chi* (invited book review) "Comprehensive
Enantioselective Organocatalysis. Edited by Peter I. Dalko". Angew. Chem. Int. Ed. 2014,
53, 6858-6859. (Online) |
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"β-Functionalization of Carboxylic Anhydrides with
β-Alkyl Substituents through Carbene Organocatalysis" |
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"N-Heterocyclic
Carbene-Catalyzed Chemoselective Cross-Aza-Benzoin Reaction of Enals with
Isatin-Derived Ketimines: Access to Chiral Quaternary Aminooxindoles". |
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"N-Heterocyclic Carbene Organocatalytic
Reductive β,β-Coupling Reactions of Nitroalkenes via Radical
Intermediates" |
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“Access to
pyridines via DMAP-catalyzed activation of α-chloro acetic ester to react
with unsaturated imines” |
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"A Family of Metal-Organic Frameworks
Exhibiting Size-Selective Catalysis with Encapsulated Noble-Metal
Nanoparticles" |
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2013 |
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“β-carbon
activation of saturated carboxylic esters through N-heterocyclic carbene
organocatalysis” |
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“Catalytic Activation of Carbohydrates as Formaldehyde
Equivalents for Stetter Reaction with Enones” |
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“Direct
β-Activation of Saturated Aldehydes to Michael Acceptors through Oxidative
NHC Catalysis” |
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“NHC Organocatalytic LUMO Activation of
α,β-Unsaturated Esters to React with Enamides” |
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“Functionalization
of Benzylic C(sp3)[BOND]H Bonds of Heteroaryl Aldehydes through
N-Heterocyclic Carbene Organocatalysis” |
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“Enantioselective Sulfonation of Enones with
Sulfonylimine via Cooperative NHC/Thiourea/Tertiary Amine Multi-Catalysis” |
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“Cis-Enals in
N-Heterocyclic Carbene-Catalyzed Reactions: Distinct Stereo-Selectivity and
Reactivity” |
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“NHC-Catalyzed Reactions of Enals with Water as
Solvent” |
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“Direct
α-Functionalization of Simple Aldehydes via Oxidative N-Heterocyclic Carbene
Catalysis” |
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“Organocatalytic Activation of Alkylacetic Esters
as Enolate Precursors to React with α,β-Unsaturated Imines” |
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“Organocatalytic
Enantioselective γ-Aminoalkylation of Unsaturated Ester: Access to Pipecolic
Acid Derivatives” |
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“Asymmetric Access to the Smallest Enolate
Intermediate via Organocatalytic Activation of Acetic Ester” |
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“Controlled β-protonation
and [4+2] cycloaddition of enals and chalcones via N-heterocyclic
carbene/acid catalysis: toward substrate independent reaction control” |
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“NHC-Catalyzed Ester Activation: Access to
Sterically Congested Spirocyclic Oxindoles via Reaction of α-Aryl Esters and
Unsaturated Imines” |
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26. Hui
Sun, Xinqiang Fang, Yonggui Robin Chi and Guohui Li “Theoretical
Study of NHC-Catalyzed Cascade Annulation of Benzodienones and Enals” |
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2012 |
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“Oxidative
γ-Addition of Enals to Trifluoromethyl Ketones: Enantioselectivity Control
via Lewis Acid/N-Heterocyclic Carbene Cooperative Catalysis” |
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“Facile Access to Chiral Ketones through Metal-Free
Oxidative C-C Bond Cleavage of Aldehydes by O2” |
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“Enantioselective
Oxidative Cross-Dehydrogenative Coupling of Tertiary Amines to Aldehydes” |
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”Addition of Indoles to Oxyallyl Cations for Facile
Access to a-Indole Carbonyl Compounds” |
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“Enantioselective
Activation of Stable Carboxylate Esters as Enolate Equivalents via
N-Heterocyclic Carbene Catalysts” |
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“Access to Spirocyclic Oxindoles via N-Heterocyclic
Carbene-Catalyzed Reactions of Enals and Oxindole-Derived α,β-Unsaturated
Imines” |
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“Enantioselective
Intramolecular Formal [2 + 4] Annulation of Acrylates and α,β-Unsaturated
Imines Catalyzed by Amino Acid Derived Phosphines” |
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“Highly Enantioselective Addition of Enals to
Isatin-Derived Ketimines Catalyzed by N-Heterocyclic Carbenes: Synthesis of
Spirocyclic γ-Lactams” |
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2011 |
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“Enantioselective
Stetter Reactions of Enals and Modified Chalcones Catalyzed by N-Heterocyclic
Carbenes” |
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“A Highly Regio- and Stereoselective Cascade
Annulation of Enals and Benzodi(enone)s Catalyzed by N-Heterocyclic Carbenes” |
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“Enantioselective
Diels–Alder Reactions of Enals and Alkylidene Diketones Catalyzed by
N-Heterocyclic Carbenes” |
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”Formal Diels-Alder Reactions of Chalcones and
Formylcyclopropanes Catalyzed by Chiral N-Heterocyclic Carbenes” |
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“Brønsted
Acid Catalyzed α-Alkylation of Aldehydes with Diaryl Methyl Alcohols” |
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Publications prior joining NTU: 12. Steven T.
Scroggins, Yonggui Chi and Jean M. J. Frechet “Polarity-Directed
One-Pot Asymmetric Cascade Reactions Mediated by Two Catalysts in Aqueous
Buffer” Angew. Chem. Int. Ed. 2010, 49, 2393-2396. 11. Li Guo, Yonggui Chi, Aaron M. Almeida, Ilia
A. Guzei, Brian K. Parker and Samuel H. Gellman “Stereospecific Synthesis
of Constrained γ-Amino Acids: New Foldamer Building Blocks Support
Helical Secondary Structure” J. Am. Chem. Soc., 2009, 131, 16018-16020. 10. Yonggui Chi, Steven T.
Scroggins, Emine Boz and Jean M. J. Frechet ”Control of Aldol
Reaction Pathways of Enolizable Aldehydes in an Aqueous Environment with a
Hyperbranched Polymeric Catalyst” J. Am. Chem.
Soc., 2008, 130, 17287–17289. 9. Yonggui
Chi, Steven T. Scroggins and Jean M. J. Frechet “One-Pot
Multi-Component Asymmetric Cascade Reactions Catalyzed by Soluble Star
Polymers with Non-Interpenetrating Catalytic Cores” J. Am. Chem. Soc., 2008, 130, 6322–6323. 8. Yonggui Chi, Li Guo, Nathan A.
Kopf and Samuel H. Gellman “Enantioselective
Organocatalytic Michael Addition of Aldehydes to Nitroethylene:
Efficient Access to γ2-Amino Acids” J. Am. Chem. Soc., 2008, 130, 5608-5609. 7. Yonggui Chi, Emily P. English,
William C. Pomerantz, W. Seth Horne, Leo A. Joyce, et. al. and
Samuel H. Gellman “Practical Synthesis
of Enantiomerically Pure β2-Amino Acids via
Proline-Catalyzed Diastereoselective Aminomethylation of
Aldehydes” J. Am. Chem. Soc., 2007, 129, 6050–6055. 6. Yonggui Chi and Samuel H. Gellman “Enantioselective
Organocatalytic Aminomethylation of Aldehydes: A Role for Ionic
Interactions and Efficient Access to β2-Amino Acids” J. Am. Chem.
Soc., 2006, 128, 6804–6805. 5. Yonggui Chi and Samuel H.
Gellman “Diphenylprolinol Methyl
Ether: A Highly Enantioselective Catalyst for Michael Addition of Aldehydes
to Simple Enones” Org. Lett., 2005,
7, 4253–4256. 4. Timothy J. Peelen, Yonggui Chi,
and Samuel H. Gellman “Enantioselective Organocatalytic
Michael Additions of Aldehydes to Enones: Cocatalyst Effects &
Evidence for an Enamine Intermediate” J. Am. Chem.
Soc., 2005, 127, 11598–11599. 3. Yonggui Chi, Timothy J. Peelen,
and Samuel H. Gellman “A Rapid 1H
NMR Assay for Enantiomeric Excess of α-Substituted Aldehydes” Org. Lett., 2005,
7, 3469–3472. 2. Timothy J. Peelen, Yonggui Chi,
Emily Payne English, and Samuel H. Gellman “Synthesis of
4,4-Disubstituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation
into 12-Helical β-Peptides” Org. Lett., 2004, 6, 4411-4414. 1. Wai-Kwok Wong, Xiao-Ping Chen,
Jian-Ping Guo, Yong-Gui Chi, Wei-Xiong Pan, Wai-Yeung Wong “Synthesis,
structure and catalytic activity of
ruthenium diaminodiphosphine complexes” J. Chem. Soc. Dalton Transations, 2002, 6, 1139-1146.
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