skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Computational Insights into the Central Role of Nonbonding Interactions in Modern Covalent Organocatalysis

Abstract

The flexibility, complexity, and size of contemporary organocatalytic transformations pose interesting and powerful opportunities to computational and experimental chemists alike. In this Account, we disclose our recent computational investigations of three branches of organocatalysis in which nonbonding interactions, such as C–H···O/N interactions, play a crucial role in the organization of transition states, catalysis, and selectivity.

Authors:
 [1];  [1];  [2];  [1]
  1. Oregon State Univ., Corvallis, OR (United States)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1337048
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
Accounts of Chemical Research
Additional Journal Information:
Journal Volume: 49; Journal Issue: 6; Journal ID: ISSN 0001-4842
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Walden, Daniel, Ogba, O. Maduka, Johnston, Ryne C., and Cheong, Paul Ha-Yeon. Computational Insights into the Central Role of Nonbonding Interactions in Modern Covalent Organocatalysis. United States: N. p., 2016. Web. https://doi.org/10.1021/acs.accounts.6b00204.
Walden, Daniel, Ogba, O. Maduka, Johnston, Ryne C., & Cheong, Paul Ha-Yeon. Computational Insights into the Central Role of Nonbonding Interactions in Modern Covalent Organocatalysis. United States. https://doi.org/10.1021/acs.accounts.6b00204
Walden, Daniel, Ogba, O. Maduka, Johnston, Ryne C., and Cheong, Paul Ha-Yeon. Mon . "Computational Insights into the Central Role of Nonbonding Interactions in Modern Covalent Organocatalysis". United States. https://doi.org/10.1021/acs.accounts.6b00204. https://www.osti.gov/servlets/purl/1337048.
@article{osti_1337048,
title = {Computational Insights into the Central Role of Nonbonding Interactions in Modern Covalent Organocatalysis},
author = {Walden, Daniel and Ogba, O. Maduka and Johnston, Ryne C. and Cheong, Paul Ha-Yeon},
abstractNote = {The flexibility, complexity, and size of contemporary organocatalytic transformations pose interesting and powerful opportunities to computational and experimental chemists alike. In this Account, we disclose our recent computational investigations of three branches of organocatalysis in which nonbonding interactions, such as C–H···O/N interactions, play a crucial role in the organization of transition states, catalysis, and selectivity.},
doi = {10.1021/acs.accounts.6b00204},
journal = {Accounts of Chemical Research},
number = 6,
volume = 49,
place = {United States},
year = {2016},
month = {6}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 21 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities
journal, August 2011

  • Cheong, Paul Ha-Yeon; Legault, Claude Y.; Um, Joann M.
  • Chemical Reviews, Vol. 111, Issue 8
  • DOI: 10.1021/cr100212h

Introduction:  Organocatalysis
journal, December 2007


Computational Organic Chemistry: Bridging Theory and Experiment in Establishing the Mechanisms of Chemical Reactions
journal, January 2015

  • Cheng, Gui-Juan; Zhang, Xinhao; Chung, Lung Wa
  • Journal of the American Chemical Society, Vol. 137, Issue 5
  • DOI: 10.1021/ja5112749

C–H⋯O non-classical hydrogen bonding in the stereomechanics of organic transformations: theory and recognition
journal, January 2013

  • Johnston, Ryne C.; Cheong, Paul Ha-Yeon
  • Organic & Biomolecular Chemistry, Vol. 11, Issue 31
  • DOI: 10.1039/c3ob40828k

A Dual-Catalysis Anion-Binding Approach to the Kinetic Resolution of Amines: Insights into the Mechanism via a Combined Experimental and Computational Study
journal, April 2015

  • Mittal, Nisha; Lippert, Katharina M.; De, Chandra Kanta
  • Journal of the American Chemical Society, Vol. 137, Issue 17
  • DOI: 10.1021/jacs.5b00190

Brønsted Acid Catalyzed Enantioselective Indole Aza-Claisen Rearrangement Mediated by an Arene CH–O Interaction
journal, October 2013

  • Maity, Pradip; Pemberton, Ryan P.; Tantillo, Dean J.
  • Journal of the American Chemical Society, Vol. 135, Issue 44
  • DOI: 10.1021/ja4095473

Influence of Hybridization and Substitution on the Properties of the CH···O Hydrogen Bond
journal, October 2001

  • Scheiner, Steve; Grabowski, Sławomir J.; Kar, Tapas
  • The Journal of Physical Chemistry A, Vol. 105, Issue 46
  • DOI: 10.1021/jp0131267

How Strong Is the C α −H···OC Hydrogen Bond?
journal, May 2000

  • Vargas, Rubicelia; Garza, Jorge; Dixon, David A.
  • Journal of the American Chemical Society, Vol. 122, Issue 19
  • DOI: 10.1021/ja993600a

An Investigation of Weak CH···O Hydrogen Bonds in Maltose Anomers by a Combination of Calculation and Experimental Solid-State NMR Spectroscopy
journal, July 2005

  • Yates, Jonathan R.; Pham, Tran N.; Pickard, Chris J.
  • Journal of the American Chemical Society, Vol. 127, Issue 29
  • DOI: 10.1021/ja051019a

The C-H.cntdot..cntdot..cntdot.O hydrogen bond in crystals: what is it?
journal, October 1991

  • Desiraju, Gautam R.
  • Accounts of Chemical Research, Vol. 24, Issue 10
  • DOI: 10.1021/ar00010a002

Intermolecular CH···O/N H-bonds in the biologically important pairs of natural nucleobases: a thorough quantum-chemical study
journal, June 2013

  • Brovarets’, Ol’ha O.; Yurenko, Yevgen P.; Hovorun, Dmytro M.
  • Journal of Biomolecular Structure and Dynamics, Vol. 32, Issue 6
  • DOI: 10.1080/07391102.2013.799439

A Case Study of the Mechanism of Alcohol-Mediated Morita Baylis–Hillman Reactions. The Importance of Experimental Observations
journal, March 2015

  • Plata, R. Erik; Singleton, Daniel A.
  • Journal of the American Chemical Society, Vol. 137, Issue 11
  • DOI: 10.1021/ja5111392

Mechanism of triflimide-catalyzed [3,3]-sigmatropic rearrangements of N-allylhydrazones—predictions and experimental validation
journal, January 2013

  • Gutierrez, Osvaldo; Strick, Benjamin F.; Thomson, Regan J.
  • Chemical Science, Vol. 4, Issue 10
  • DOI: 10.1039/c3sc51564h

Origins of Differences in Reactivities of Alkenes, Alkynes, and Allenes in [Rh(CO) 2 Cl] 2 -Catalyzed (5 + 2) Cycloaddition Reactions with Vinylcyclopropanes
journal, February 2008

  • Yu, Zhi-Xiang; Cheong, Paul Ha-Yeon; Liu, Peng
  • Journal of the American Chemical Society, Vol. 130, Issue 8
  • DOI: 10.1021/ja076444d

Does Substrate Oxidation Determine the Regioselectivity of Cyclohexene and Propene Oxidation by Cytochrome P450?
journal, August 2006

  • Cohen, Shimrit; Kozuch, Sebastian; Hazan, Carina
  • Journal of the American Chemical Society, Vol. 128, Issue 34
  • DOI: 10.1021/ja063269c

The Activated Complex in Chemical Reactions
journal, February 1935

  • Eyring, Henry
  • The Journal of Chemical Physics, Vol. 3, Issue 2
  • DOI: 10.1063/1.1749604

Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993

  • Becke, Axel D.
  • The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
  • DOI: 10.1063/1.464913

Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
journal, January 1988


Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy
journal, January 2005

  • Weigend, Florian; Ahlrichs, Reinhart
  • Physical Chemistry Chemical Physics, Vol. 7, Issue 18, p. 3297-3305
  • DOI: 10.1039/b508541a

Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules
journal, March 1972

  • Hehre, W. J.; Ditchfield, R.; Pople, J. A.
  • The Journal of Chemical Physics, Vol. 56, Issue 5, p. 2257-2261
  • DOI: 10.1063/1.1677527

The influence of polarization functions on molecular orbital hydrogenation energies
journal, January 1973

  • Hariharan, P. C.; Pople, J. A.
  • Theoretica Chimica Acta, Vol. 28, Issue 3
  • DOI: 10.1007/BF00533485

Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions
journal, May 2009

  • Marenich, Aleksandr V.; Cramer, Christopher J.; Truhlar, Donald G.
  • The Journal of Physical Chemistry B, Vol. 113, Issue 18, p. 6378-6396
  • DOI: 10.1021/jp810292n

Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes
journal, May 2015

  • Flanigan, Darrin M.; Romanov-Michailidis, Fedor; White, Nicholas A.
  • Chemical Reviews, Vol. 115, Issue 17
  • DOI: 10.1021/acs.chemrev.5b00060

Dynamic resolutions in asymmetric synthesis
journal, January 1996


Asymmetric Organic Catalysis with Modified Cinchona Alkaloids
journal, May 2004

  • Tian, Shi-Kai; Chen, Yonggang; Hang, Jianfeng
  • Accounts of Chemical Research, Vol. 37, Issue 8
  • DOI: 10.1021/ar030048s

Catalytic Dynamic Kinetic Resolutions with N-Heterocyclic Carbenes: Asymmetric Synthesis of Highly Substituted β-Lactones
journal, June 2012

  • Cohen, Daniel T.; Eichman, Chad C.; Phillips, Eric M.
  • Angewandte Chemie International Edition, Vol. 51, Issue 29
  • DOI: 10.1002/anie.201203382

Catalytic kinetic resolution of a dynamic racemate: highly stereoselective β-lactone formation by N-heterocyclic carbene catalysis
journal, January 2014

  • Johnston, Ryne C.; Cohen, Daniel T.; Eichman, Chad C.
  • Chem. Sci., Vol. 5, Issue 5
  • DOI: 10.1039/c4sc00317a

Asymmetric Synthesis of Bicyclic β-Lactones via the Intramolecular, Nucleophile-Catalyzed Aldol Lactonization:  Improved Efficiency and Expanded Scope
journal, February 2005

  • Oh, Seong Ho; Cortez, Guillermo S.; Romo, Daniel
  • The Journal of Organic Chemistry, Vol. 70, Issue 7
  • DOI: 10.1021/jo050024u

Synthetic and Quantum Mechanical Studies into the N- Heterocyclic Carbene Catalyzed (4 + 2) Cycloaddition
journal, January 2012

  • Ryan, Sarah J.; Stasch, Andreas; Paddon-Row, Michael N.
  • The Journal of Organic Chemistry, Vol. 77, Issue 2
  • DOI: 10.1021/jo202500k

Intrinsic reaction coordinate: Calculation, bifurcation, and automated search
journal, September 2014

  • Maeda, Satoshi; Harabuchi, Yu; Ono, Yuriko
  • International Journal of Quantum Chemistry, Vol. 115, Issue 5
  • DOI: 10.1002/qua.24757

Asymmetric Homoenolate Additions to Acyl Phosphonates through Rational Design of a Tailored N -Heterocyclic Carbene Catalyst
journal, December 2013

  • Jang, Ki Po; Hutson, Gerri E.; Johnston, Ryne C.
  • Journal of the American Chemical Society, Vol. 136, Issue 1
  • DOI: 10.1021/ja410932t

Asymmetric Conjugate Addition of Silyl Enol Ethers Catalyzed by Tethered Bis(8-quinolinolato) Aluminum Complexes
journal, January 2007

  • Takenaka, Norito; Abell, Joshua P.; Yamamoto, Hisashi
  • Journal of the American Chemical Society, Vol. 129, Issue 4
  • DOI: 10.1021/ja0668320

Enantioselective Indole Friedel−Crafts Alkylations Catalyzed by Bis(oxazolinyl)pyridine−Scandium(III) Triflate Complexes
journal, September 2003

  • Evans, David A.; Scheidt, Karl A.; Fandrick, Keith R.
  • Journal of the American Chemical Society, Vol. 125, Issue 36
  • DOI: 10.1021/ja036985c

Catalytic Enantioselective Hetero Diels−Alder Reactions of α,β-Unsaturated Acyl Phosphonates with Enol Ethers
journal, May 1998

  • Evans, David A.; Johnson, Jeffrey S.
  • Journal of the American Chemical Society, Vol. 120, Issue 19
  • DOI: 10.1021/ja980423p

Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates: synthetic and computational studies
journal, January 2014

  • Gould, Eoin; Walden, Daniel M.; Kasten, Kevin
  • Chemical Science, Vol. 5, Issue 9
  • DOI: 10.1039/C4SC00879K

4-Dialkylaminopyridines as Highly Active Acylation Catalysts. [New synthetic method (25)]
journal, August 1978

  • Höfle, Gerhard; Steglich, Wolfgang; Vorbrüggen, Helmut
  • Angewandte Chemie International Edition in English, Vol. 17, Issue 8
  • DOI: 10.1002/anie.197805691

Enantioselective Construction of Quaternary Stereocenters:  Rearrangements of O -Acylated Azlactones Catalyzed by a Planar-Chiral Derivative of 4-(Pyrrolidino)pyridine
journal, November 1998

  • Ruble, J. Craig; Fu, Gregory C.
  • Journal of the American Chemical Society, Vol. 120, Issue 44
  • DOI: 10.1021/ja982890c

Development of Chiral Nucleophilic Pyridine Catalysts:  Applications in Asymmetric Quaternary Carbon Synthesis
journal, November 2003

  • Shaw, Scott A.; Aleman, Pedro; Vedejs, Edwin
  • Journal of the American Chemical Society, Vol. 125, Issue 44
  • DOI: 10.1021/ja037223k

Efficient N-Heterocyclic Carbene-Catalyzed O - to C-Acyl Transfer
journal, August 2006

  • Thomson, Jennifer E.; Rix, Kathryn; Smith, Andrew D.
  • Organic Letters, Vol. 8, Issue 17
  • DOI: 10.1021/ol061380h

Enantioselective Steglich Rearrangement of Oxindole Derivatives by Easily Accessible Chiral N , N -4-(Dimethylamino)pyridine Derivatives
journal, September 2015


Catalytic Enantioselective Synthesis of Oxindoles and Benzofuranones That Bear a Quaternary Stereocenter
journal, August 2003

  • Hills, Ivory D.; Fu, Gregory C.
  • Angewandte Chemie International Edition, Vol. 42, Issue 33
  • DOI: 10.1002/anie.200351666

The DMAP-Catalyzed Acetylation of Alcohols—A Mechanistic Study (DMAP=4-(Dimethylamino)pyridine)
journal, August 2005

  • Xu, Shangjie; Held, Ingmar; Kempf, Bernhard
  • Chemistry - A European Journal, Vol. 11, Issue 16
  • DOI: 10.1002/chem.200500398

Chiral Dialkylaminopyridine Catalysts in Asymmetric Synthesis
journal, December 2007


Ketenes and Other Cumulenes as Reactive Intermediates
journal, June 2013

  • Allen, Annette D.; Tidwell, Thomas T.
  • Chemical Reviews, Vol. 113, Issue 9
  • DOI: 10.1021/cr3005263

Enantioselective Addition of Amines to Ketenes Catalyzed by a Planar-Chiral Derivative of PPY:  Possible Intervention of Chiral Brønsted-Acid Catalysis
journal, August 2002

  • Hodous, Brian L.; Fu, Gregory C.
  • Journal of the American Chemical Society, Vol. 124, Issue 34
  • DOI: 10.1021/ja027466x

Mechanism and Stereocontrol: Enantioselective Addition of Pyrrole to Ketenes Using Planar-Chiral Organocatalysts
journal, December 2012

  • Pattawong, Ommidala; Mustard, Thomas J. L.; Johnston, Ryne C.
  • Angewandte Chemie International Edition, Vol. 52, Issue 5
  • DOI: 10.1002/anie.201208417

Calculation of Equilibrium Constants for Isotopic Exchange Reactions
journal, May 1947

  • Bigeleisen, Jacob; Mayer, Maria Goeppert
  • The Journal of Chemical Physics, Vol. 15, Issue 5
  • DOI: 10.1063/1.1746492

Nucleophilic Chiral Amines as Catalysts in Asymmetric Synthesis
journal, August 2003

  • France, Stefan; Guerin, David J.; Miller, Scott J.
  • Chemical Reviews, Vol. 103, Issue 8
  • DOI: 10.1021/cr020061a

Stereoselective Construction of Quaternary Carbon Stereocenters via a Semipinacol Rearrangement Strategy
journal, November 2011

  • Wang, Baomin; Tu, Yong Qiang
  • Accounts of Chemical Research, Vol. 44, Issue 11
  • DOI: 10.1021/ar200082p

The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters
journal, March 1998


Asymmetric creation of quaternary carbon centers
journal, September 1993


Enantioselective synthesis of quaternary carbon centers through Michael-type alkylation of chiral imines
journal, January 1985

  • Pfau, Michel; Revial, Gilbert; Guingant, Andre
  • Journal of the American Chemical Society, Vol. 107, Issue 1
  • DOI: 10.1021/ja00287a061

Asymmetric Catalysis by Chiral Hydrogen-Bond Donors
journal, February 2006

  • Taylor, Mark S.; Jacobsen, Eric N.
  • Angewandte Chemie International Edition, Vol. 45, Issue 10
  • DOI: 10.1002/anie.200503132

Metal-free organocatalysis through explicit hydrogen bonding interactions
journal, January 2003

  • Schreiner, Peter R.
  • Chemical Society Reviews, Vol. 32, Issue 5
  • DOI: 10.1039/b107298f

Construction of Stereogenic α,α-Disubstituted Cycloalkanones via 1° Amine Thiourea Dual Catalysis: Experimental Scope and Computational Analyses
journal, April 2016

  • Kang, Jun Yong; Johnston, Ryne C.; Snyder, Kevin M.
  • The Journal of Organic Chemistry, Vol. 81, Issue 9
  • DOI: 10.1021/acs.joc.6b00280

Chiral Thiourea-Based Bifunctional Organocatalysts in the Asymmetric Nitro-Michael Addition: A Joint Experimental-Theoretical Study
journal, May 2006

  • Yalalov, Denis A.; Tsogoeva, Svetlana B.; Schmatz, Stefan
  • Advanced Synthesis & Catalysis, Vol. 348, Issue 7-8
  • DOI: 10.1002/adsc.200505443

Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts
journal, October 2003

  • Okino, Tomotaka; Hoashi, Yasutaka; Takemoto, Yoshiji
  • Journal of the American Chemical Society, Vol. 125, Issue 42
  • DOI: 10.1021/ja036972z

Bifunctional primary amine-thioureas in asymmetric organocatalysis
journal, January 2013

  • Serdyuk, Olga V.; Heckel, Christina M.; Tsogoeva, Svetlana B.
  • Organic & Biomolecular Chemistry, Vol. 11, Issue 41
  • DOI: 10.1039/c3ob41403e

Asymmetric synthesis of bicyclic intermediates of natural product chemistry
journal, June 1974

  • Hajos, Zoltan G.; Parrish, David R.
  • The Journal of Organic Chemistry, Vol. 39, Issue 12
  • DOI: 10.1021/jo00925a003

Enamine-Based Organocatalysis with Proline and Diamines:  The Development of Direct Catalytic Asymmetric Aldol, Mannich, Michael, and Diels−Alder Reactions
journal, August 2004

  • Notz, Wolfgang; Tanaka, Fujie; Barbas, Carlos F.
  • Accounts of Chemical Research, Vol. 37, Issue 8
  • DOI: 10.1021/ar0300468

Proline-catalyzed asymmetric reactions
journal, July 2002


Rate Limiting Step Precedes C−C Bond Formation in the Archetypical Proline-Catalyzed Intramolecular Aldol Reaction
journal, January 2009

  • Zhu, Hui; Clemente, Fernando R.; Houk, K. N.
  • Journal of the American Chemical Society, Vol. 131, Issue 5
  • DOI: 10.1021/ja806672y

Clarification of the Role of Water in Proline-Mediated Aldol Reactions
journal, November 2007

  • Zotova, Natalia; Franzke, Axel; Armstrong, Alan
  • Journal of the American Chemical Society, Vol. 129, Issue 49
  • DOI: 10.1021/ja0738881

Theory of Asymmetric Organocatalysis of Aldol and Related Reactions:  Rationalizations and Predictions
journal, July 2004

  • Allemann, Christophe; Gordillo, Ruth; Clemente, Fernando R.
  • Accounts of Chemical Research, Vol. 37, Issue 8
  • DOI: 10.1021/ar0300524

Computational Evidence for the Enamine Mechanism of Intramolecular Aldol Reactions Catalyzed by Proline
journal, November 2004

  • Clemente, Fernando R.; Houk, K. N.
  • Angewandte Chemie International Edition, Vol. 43, Issue 43
  • DOI: 10.1002/anie.200460916

The Origin of Stereoselectivity in Proline-Catalyzed Intramolecular Aldol Reactions
journal, December 2001

  • Bahmanyar, S.; Houk, K. N.
  • Journal of the American Chemical Society, Vol. 123, Issue 51
  • DOI: 10.1021/ja011714s

Mechanism and Stereoselectivity of a Dual Amino-Catalyzed Robinson Annulation: Rare Duumvirate Stereocontrol
journal, August 2012

  • Pierce, Matthew D.; Johnston, Ryne C.; Mahapatra, Subham
  • Journal of the American Chemical Society, Vol. 134, Issue 33
  • DOI: 10.1021/ja3018219

    Works referencing / citing this record:

    Isothiourea-catalysed enantioselective pyrrolizine synthesis: synthetic and computational studies
    journal, January 2016

    • Stark, Daniel G.; Williamson, Patrick; Gayner, Emma R.
    • Organic & Biomolecular Chemistry, Vol. 14, Issue 38
    • DOI: 10.1039/C6OB01557C

    Cobalt-catalyzed C–H cyanations: Insights into the reaction mechanism and the role of London dispersion
    journal, January 2018

    • Detmar, Eric; Müller, Valentin; Zell, Daniel
    • Beilstein Journal of Organic Chemistry, Vol. 14
    • DOI: 10.3762/bjoc.14.130

    Competing mechanisms and origins of chemo- and stereo-selectivities of NHC-catalyzed reactions of enals with 2-aminoacrylates
    journal, January 2018

    • Wang, Yang; Wang, Yanyan; Wang, Xinghua
    • Catalysis Science & Technology, Vol. 8, Issue 16
    • DOI: 10.1039/c8cy01272e

    Catalytic Generation of Donor-Acceptor Cyclopropanes under N -Heterocyclic Carbene Activation and their Stereoselective Reaction with Alkylideneoxindoles
    journal, April 2017

    • Prieto, Liher; Sánchez-Díez, Eduardo; Uria, Uxue
    • Advanced Synthesis & Catalysis, Vol. 359, Issue 10
    • DOI: 10.1002/adsc.201700198

    Stacking and Electrostatic Interactions Drive the Stereoselectivity of Silylium-Ion Asymmetric Counteranion-Directed Catalysis
    journal, November 2016


    C( sp 2 )−H Hydrogen‐Bond Donor Groups in Chiral Small‐Molecule Organocatalysts
    journal, June 2019

    • Reep, Carlyn; Sun, Shiyu; Takenaka, Norito
    • Asian Journal of Organic Chemistry, Vol. 8, Issue 8
    • DOI: 10.1002/ajoc.201900122

    Stacking and Electrostatic Interactions Drive the Stereoselectivity of Silylium-Ion Asymmetric Counteranion-Directed Catalysis
    journal, November 2016

    • Seguin, Trevor J.; Wheeler, Steven E.
    • Angewandte Chemie International Edition, Vol. 55, Issue 51
    • DOI: 10.1002/anie.201609095

    Stereodivergent Aminocatalytic Synthesis of Z - and E -Trisubstituted Double Bonds from Alkynals
    journal, October 2016

    • Marzo, Leyre; Luis-Barrera, Javier; Mas-Ballesté, Rubén
    • Chemistry - A European Journal, Vol. 22, Issue 46
    • DOI: 10.1002/chem.201603437

    H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins
    journal, January 2020

    • Ding, Pei-Gang; Zhou, Feng; Wang, Xin
    • Chemical Science, Vol. 11, Issue 15
    • DOI: 10.1039/d0sc00475h

    A Counterion-Directed Approach to the Diels-Alder Paradigm: Cascade Synthesis of Tricyclic Fused Cyclopropanes
    journal, October 2016

    • Kiss, Emily; Campbell, Craig D.; Driver, Russell W.
    • Angewandte Chemie International Edition, Vol. 55, Issue 44
    • DOI: 10.1002/anie.201608534