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

CORDIS provides links to public deliverables and publications of HORIZON projects.

Links to deliverables and publications from FP7 projects, as well as links to some specific result types such as dataset and software, are dynamically retrieved from OpenAIRE .

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