C-H Acids for Organic Synthesis

Project Information

CHAOS

Grant agreement ID: 694228

DOI 10.3030/694228

Project closed

EC signature date 29 April 2016

Start date 1 October 2016

End date 30 September 2021

Funded under

• EXCELLENT SCIENCE - European Research Council (ERC)

Total cost € 2 007 500,00

EU contribution € 2 007 500,00

Coordinated by

MAX PLANCK INSTITUT FUER KOHLENFORSCHUNG
Germany

Publications

Peer reviewed articles (45)

Catalytic Asymmetric Hydroalkoxylation of C–C Multiple Bonds

Author(s): Kennemur, J. L., Maji, R., Scharf, M. J., List, Benjamin
Published in: Chem. Rev. 2021, 121, 24, 14649–14681, Issue 121(24), 2021, Page(s) 14649-14681, ISSN 0009-2665
Publisher: American Chemical Society
DOI: 10.1021/acs.chemrev.1c00620

Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo‐Diaza‐Cope Rearrangement

Author(s): Gabriela Guillermina Gerosa, Sebastian Armin Schwengers, Rajat Maji, Chandra Kanta De, Benjamin List
Published in: Angewandte Chemie International Edition, Issue 59/46, 2020, Page(s) 20485-20488, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202005798

Chiral Brønsted Acids Catalyze Asymmetric Additions to Substrates that Are Already Protonated: Highly Enantioselective Disulfonimide-Catalyzed Hantzsch Ester Reductions of NH–Imine Hydrochloride Salts

Author(s): Wakchaure Vijay N., Obradors Carla, List Benjamin
Published in: Synlett, Issue 31 (17), 2020, Page(s) 1707 - 1712, ISSN 0936-5214
Publisher: Georg Thieme Verlag
DOI: 10.1055/s-0040-1706413

A Chiral Sulfoxide-Based C–H Acid

Author(s): List, B., Höfler, D., Kaupmees, K., & Leito, I
Published in: Synlett 2022; 33(01): 45-47, Issue 33(01), 2021, Page(s) 45-47, ISSN 0936-5214
Publisher: Georg Thieme Verlag
DOI: 10.1055/a-1695-4516

Organocatalysis emerging as a technology

Author(s): Aukland, Miles. H., List, Benjamin
Published in: Pure and Applied Chemistry, Issue 93(12), 2021, Page(s) 1371-1381, ISSN 0033-4545
Publisher: International Union of Pure and Applied Chemistry
DOI: 10.1515/pac-2021-0501

Unified Approach to Imidodiphosphate-Type Brønsted Acids with Tunable Confinement and Acidity

Author(s): Sebastian A. Schwengers, Chandra Kanta De, Oleg Grossmann, Joyce A. A. Grimm, Natascha R. Sadlowski, Gabriela G. Gerosa, and Benjamin List
Published in: Journal of the American Chemical Society, Issue 143(36), 2021, Page(s) 14835-14844, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.1c07067

Catalytic Asymmetric Additions of Enol Silanes to in situ Generated Cyclic, Aliphatic N-Acyliminium Ions

Author(s): Grossmann, Oleg., Maji, Rajat., Aukland, Miles. H., Lee, Sunggi., List, Benjamin
Published in: Angewandte Chemie International Edition, 2021, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202115036

Azine Activation via Silylium Catalysis

Author(s): Obradors Carla, Benjamin List
Published in: Journal of the American Chemical Society, Issue 143(18), 2021, Page(s) 6817-6822, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.1c03257

Harnessing the ambiphilicity of silyl nitronates in a catalytic asymmetric approach to aliphatic β3-amino acids

Author(s): Das, S., Mitschke, Benjamin., De, C. K., Harden, I., Bistoni, G.,List, Benjamin
Published in: Nature Catalysis, Issue 4(12), 2021, Page(s) 1043-1049, ISSN 2520-1158
Publisher: New York : Nature Publishing Group
DOI: 10.1038/s41929-021-00714-x

Confinement as a Unifying Element in Selective Catalysis

Author(s): Benjamin Mitschke, Mathias Turberg and Benjamin List
Published in: Chem, Issue 6(10), 2020, Page(s) 2515-2532, ISSN 2451-9294
Publisher: Elservier
DOI: 10.1016/j.chempr.2020.09.007

Catalytic Asymmetric Synthesis of Unprotected β 2 -Amino Acids

Author(s): Chendan Zhu, Francesca Mandrelli, Hui Zhou, Rajat Maji, Benjamin List
Published in: Journal of the American Chemical Society, Issue 143/9, 2021, Page(s) 3312-3317, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.1c00249

The Silicon–Hydrogen Exchange Reaction: Catalytic Kinetic Resolution of 2-Substituted Cyclic Ketones

Author(s): Hui Zhou, Pinglu Zhang, Benjamin List
Published in: Synlett 2022; 33(01): 38-39, Issue 33(01), 2021, Page(s) 38-39, ISSN 0936-5214
Publisher: Georg Thieme Verlag
DOI: 10.1055/a-1670-5829

Confinement-Controlled, Either syn- or anti-Selective Catalytic Asymmetric Mukaiyama Aldolizations of Propionaldehyde Enolsilanes

Author(s): Tynchtyk Amatov, Nobuya Tsuji, Rajat Maji, Lucas Schreyer, Hui Zhou, Markus Leutzsch, and Benjamin List
Published in: Journal of the American Chemical Society, Issue 143 (36), 2021, Page(s) 14475-14481, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.1c07447

Organocatalytic stereoselective cyanosilylation of small ketones

Author(s): Hui Zhou, Yu Zhou, Han Yong Bae, Markus Leutzsch, Yihang Li, Chandra Kanta De, Gui-Juan Cheng & Benjamin List1
Published in: Nature, Issue 605, 2022, Page(s) 84 - 89, ISSN 2520-1158
Publisher: Nature Publishing Group
DOI: 10.1038/s41586-022-04531-5

Catalytic Asymmetric Spirocyclizing Diels–Alder Reactions of Enones: Stereoselective Total and Formal Syntheses of α-Chamigrene, β-Chamigrene, Laurencenone C, Colletoic Acid, and Omphalic Acid

Author(s): Ghosh, S., Erchinger, J. E., Maji, R., List, B.
Published in: Journal of the American Chemical Society, Issue 144 (15), 2022, Page(s) 6703 - 6708, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.2c01971

The Smelling Principle of Vetiver Oil, Unveiled by Chemical Synthesis

Author(s): Jie Ouyang, Hanyong Bae, Samuel Jordi, Quang Minh Dao, Sandro Dossenbach, Stefanie Dehn, Julia B. Lingnau, Chandra Kanta De, Philip Kraft, Benjamin List
Published in: Angewandte Chemie International Edition, Issue 60/11, 2021, Page(s) 5666-5672, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202014609

Catalytic Asymmetric Intramolecular [4+2] Cycloaddition of In Situ Generated ortho -Quinone Methides

Author(s): Youwei Xie, Benjamin List
Published in: Angewandte Chemie International Edition, Issue 56/18, 2017, Page(s) 4936-4940, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201612149

High Lithium Transference Number Electrolytes Containing Tetratriflylpropene’s Lithium Salt

Author(s): J. Popovic, D. Höfler, J. P. Melchior, A. Münchinger, B. List, J. Maier
Published in: The Journal of Physical Chemistry Letters, Issue 9/17, 2018, Page(s) 5116-5120, ISSN 1948-7185
Publisher: American Chemical Society
DOI: 10.1021/acs.jpclett.8b01846

Approaching sub-ppm-level asymmetric organocatalysis of a highly challenging and scalable carbon–carbon bond forming reaction

Author(s): Han Yong Bae, Denis Höfler, Philip S. J. Kaib, Pinar Kasaplar, Chandra Kanta De, Arno Döhring, Sunggi Lee, Karl Kaupmees, Ivo Leito, Benjamin List
Published in: Nature Chemistry, Issue 10/8, 2018, Page(s) 888-894, ISSN 1755-4330
Publisher: Nature Publishing Group
DOI: 10.1038/s41557-018-0065-0

A Dendralenic C–H Acid

Author(s): Denis Höfler, Richard Goddard, Nils Nöthling, Benjamin List
Published in: Synlett, Issue 30/04, 2019, Page(s) 433-436, ISSN 0936-5214
Publisher: Georg Thieme Verlag
DOI: 10.1055/s-0037-1612246

Triflimide: An Overlooked High-Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones

Author(s): Han Yong Bae, Benjamin List
Published in: Chemistry - A European Journal, Issue 24/52, 2018, Page(s) 13767-13772, ISSN 0947-6539
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/chem.201803142

A multi-substrate screening approach for the identification of a broadly applicable Diels–Alder catalyst

Author(s): Hyejin Kim, Gabriela Gerosa, Jonas Aronow, Pinar Kasaplar, Jie Ouyang, Julia B. Lingnau, Paul Guerry, Christophe Farès, Benjamin List
Published in: Nature Communications, Issue 10/1, 2019, Page(s) 770, ISSN 2041-1723
Publisher: Nature Publishing Group
DOI: 10.1038/s41467-019-08374-z

Scalable and Highly Diastereo- and Enantioselective Catalytic Diels–Alder Reaction of α,β-Unsaturated Methyl Esters

Author(s): Tim Gatzenmeier, Mathias Turberg, Diana Yepes, Youwei Xie, Frank Neese, Giovanni Bistoni, Benjamin List
Published in: Journal of the American Chemical Society, Issue 140/40, 2018, Page(s) 12671-12676, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.8b07092

Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates

Author(s): Lucas Schreyer, Philip S. J. Kaib, Vijay N. Wakchaure, Carla Obradors, Roberta Properzi, Sunggi Lee, Benjamin List
Published in: Science, Issue 362/6411, 2018, Page(s) 216-219, ISSN 0036-8075
Publisher: American Association for the Advancement of Science
DOI: 10.1126/science.aau0817

Strong and Confined Acids Enable a Catalytic Asymmetric Nazarov Cyclization of Simple Divinyl Ketones

Author(s): Jie Ouyang, Jennifer L. Kennemur, Chandra Kanta De, Christophe Farès, Benjamin List
Published in: Journal of the American Chemical Society, Issue 141/8, 2019, Page(s) 3414-3418, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.8b13899

Can a Ketone Be More Reactive than an Aldehyde? Catalytic Asymmetric Synthesis of Substituted Tetrahydrofurans

Author(s): Sunggi Lee, Han Yong Bae, Benjamin List
Published in: Angewandte Chemie International Edition, Issue 57/37, 2018, Page(s) 12162-12166, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201806312

Design and Synthesis of Enantiopure Tetrakis(pentafluorophenyl) Borate Analogues for Asymmetric Counteranion Directed Catalysis

Author(s): Benjamin List, Chandra De, Raja Mitra
Published in: Synlett, Issue 28/18, 2017, Page(s) 2435-2438, ISSN 0936-5214
Publisher: Georg Thieme Verlag
DOI: 10.1055/s-0036-1590903

Activation of olefins via asymmetric Brønsted acid catalysis

Author(s): Nobuya Tsuji, Jennifer L. Kennemur, Thomas Buyck, Sunggi Lee, Sébastien Prévost, Philip S. J. Kaib, Dmytro Bykov, Christophe Farès, Benjamin List
Published in: Science, Issue 359/6383, 2018, Page(s) 1501-1505, ISSN 0036-8075
Publisher: American Association for the Advancement of Science
DOI: 10.1126/science.aaq0445

A Purely Organic Tricarbanion

Author(s): Denis Höfler, Richard Goddard, Julia B. Lingnau, Nils Nöthling, Benjamin List
Published in: Angewandte Chemie International Edition, Issue 57/27, 2018, Page(s) 8326-8329, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201803647

N-Triflylphosphorimidoyl Trichloride: A Versatile Reagent for the Synthesis of Strong Chiral Brønsted Acids

Author(s): Benjamin List, Sunggi Lee, Philip Kaib
Published in: Synlett, Issue 28/12, 2017, Page(s) 1478-1480, ISSN 0936-5214
Publisher: Georg Thieme Verlag
DOI: 10.1055/s-0036-1588782

1,1,3,3-Tetratriflylpropene (TTP): A Strong, Allylic C-H Acid for Brønsted and Lewis Acid Catalysis

Author(s): Denis Höfler, Manuel van Gemmeren, Petra Wedemann, Karl Kaupmees, Ivo Leito, Markus Leutzsch, Julia B. Lingnau, Benjamin List
Published in: Angewandte Chemie International Edition, Issue 56/5, 2017, Page(s) 1411-1415, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201609923

Asymmetric Catalysis of the Carbonyl-Amine Condensation: Kinetic Resolution of Primary Amines

Author(s): Sayantani Das, Nilanjana Majumdar, Chandra Kanta De, Dipti Sankar Kundu, Arno Döhring, Anika Garczynski, Benjamin List
Published in: Journal of the American Chemical Society, Issue 139/4, 2017, Page(s) 1357-1359, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.6b12176

The Catalytic Asymmetric Mukaiyama-Michael Reaction of Silyl Ketene Acetals with α,β-Unsaturated Methyl Esters

Author(s): Tim Gatzenmeier, Philip S. J. Kaib, Julia B. Lingnau, Richard Goddard, Benjamin List
Published in: Angewandte Chemie International Edition, Issue 57/9, 2018, Page(s) 2464-2468, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201712088

Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions

Author(s): Sunggi Lee, Philip S. J. Kaib, Benjamin List
Published in: Journal of the American Chemical Society, Issue 139/6, 2017, Page(s) 2156-2159, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.6b11993

Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes

Author(s): Luping Liu, Hyejin Kim, Youwei Xie, Christophe Farès, Philip S. J. Kaib, Richard Goddard, Benjamin List
Published in: Journal of the American Chemical Society, Issue 139/39, 2017, Page(s) 13656-13659, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.7b08357

Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol

Author(s): Francesca Mandrelli, Aurélie Blond, Thomas James, Hyejin Kim, Benjamin List
Published in: Angewandte Chemie International Edition, Issue 58/33, 2019, Page(s) 11479-11482, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201905623

IDPi Catalysis

Author(s): Schreyer Lucas, Properzi Roberta, List Benjamin
Published in: Angewandte Chemie International Edition, Issue 58(37), 2019, Page(s) 12761-12777, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201900932

Strong and Confined Acids Catalyze Asymmetric Intramolecular Hydroarylations of Unactivated Olefins with Indoles

Author(s): Pinglu Zhang, Nobuya Tsuji, Jie Ouyang, Benjamin List
Published in: Journal of the American Chemical Society, Issue 143/2, 2021, Page(s) 675-680, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.0c12042

The Catalytic Asymmetric Intermolecular Prins Reaction

Author(s): Díaz-Oviedo, C. David., Maji, Rajat.,List, Benjamin
Published in: J. Am. Chem. Soc. 2021, 143, 49, 20598, Issue 143(49), 2021, Page(s) 20598-20604, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.1c10245

Direct and Catalytic C-Glycosylation of Arenes: Expeditious Synthesis of the Remdesivir Nucleoside

Author(s): Obradors, C., Mitschke, B., Aukland, M. H., Leutzsch, M., Grossmann, O., Brunen, S., Schwengers, Sebastian., List, Benjamin
Published in: Angewandte Chemie International Edition, 2021, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202114619

Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes

Author(s): Ouyang, J., Maji, R., Leutzsch, M., Mitschke, B., & List, B.
Published in: Journal of the American Chemical Society, Issue 144 (19), 2022, Page(s) 8460 - 8466, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.2c02216

A Chiral, Dendralenic C–H Acid

Author(s): Höfler, Dennis., & List, Benjamin
Published in: Synlett 2022; 33(01): 38-39, Issue 33(01), 2021, Page(s) 38-39, ISSN 0936-5214
Publisher: Georg Thieme Verlag
DOI: 10.1055/a-1705-9786

The Silicon–Hydrogen Exchange Reaction: A Catalytic σ-Bond Metathesis Approach to the Enantioselective Synthesis of Enol Silanes

Author(s): Hui Zhou, Han Yong Bae, Markus Leutzsch, Jennifer L. Kennemur, Diane Bécart, Benjamin List
Published in: Journal of the American Chemical Society, Issue 142/32, 2020, Page(s) 13695-13700, ISSN 0002-7863
Publisher: American Chemical Society
DOI: 10.1021/jacs.0c06677

Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene

Author(s): Santanu Ghosh, Sayantani Das, Chandra Kanta De, Diana Yepes, Frank Neese, Giovanni Bistoni, Markus Leutzsch, Benjamin List
Published in: Angewandte Chemie International Edition, Issue 59/30, 2020, Page(s) 12347-12351, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202000307

Catalytic enantiocontrol over a non-classical carbocation

Author(s): Roberta Properzi, Philip S. J. Kaib, Markus Leutzsch, Gabriele Pupo, Raja Mitra, Chandra Kanta De, Lijuan Song, Peter R. Schreiner and Benjamin List*
Published in: Nature Chemistry, Issue 12, 2020, Page(s) 1174-1179, ISSN 1755-4330
Publisher: Nature Publishing Group
DOI: 10.1038/s41557-020-00558-1