C-H Acids for Organic Synthesis

Informazioni relative al progetto

CHAOS

ID dell’accordo di sovvenzione: 694228

DOI 10.3030/694228

Progetto chiuso

Data della firma CE 29 Aprile 2016

Data di avvio 1 Ottobre 2016

Data di completamento 30 Settembre 2021

Finanziato da

• EXCELLENT SCIENCE - European Research Council (ERC)

Costo totale € 2 007 500,00

Contributo UE € 2 007 500,00

Coordinato da

MAX PLANCK INSTITUT FUER KOHLENFORSCHUNG
Germany

Pubblicazioni

Peer reviewed articles (45)

Catalytic Asymmetric Hydroalkoxylation of C–C Multiple Bonds

Autori: Kennemur, J. L., Maji, R., Scharf, M. J., List, Benjamin
Pubblicato in: Chem. Rev. 2021, 121, 24, 14649–14681, Numero 121(24), 2021, Pagina/e 14649-14681, ISSN 0009-2665
Editore: American Chemical Society
DOI: 10.1021/acs.chemrev.1c00620

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

Autori: Gabriela Guillermina Gerosa, Sebastian Armin Schwengers, Rajat Maji, Chandra Kanta De, Benjamin List
Pubblicato in: Angewandte Chemie International Edition, Numero 59/46, 2020, Pagina/e 20485-20488, ISSN 1433-7851
Editore: 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

Autori: Wakchaure Vijay N., Obradors Carla, List Benjamin
Pubblicato in: Synlett, Numero 31 (17), 2020, Pagina/e 1707 - 1712, ISSN 0936-5214
Editore: Georg Thieme Verlag
DOI: 10.1055/s-0040-1706413

A Chiral Sulfoxide-Based C–H Acid

Autori: List, B., Höfler, D., Kaupmees, K., & Leito, I
Pubblicato in: Synlett 2022; 33(01): 45-47, Numero 33(01), 2021, Pagina/e 45-47, ISSN 0936-5214
Editore: Georg Thieme Verlag
DOI: 10.1055/a-1695-4516

Organocatalysis emerging as a technology

Autori: Aukland, Miles. H., List, Benjamin
Pubblicato in: Pure and Applied Chemistry, Numero 93(12), 2021, Pagina/e 1371-1381, ISSN 0033-4545
Editore: 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

Autori: Sebastian A. Schwengers, Chandra Kanta De, Oleg Grossmann, Joyce A. A. Grimm, Natascha R. Sadlowski, Gabriela G. Gerosa, and Benjamin List
Pubblicato in: Journal of the American Chemical Society, Numero 143(36), 2021, Pagina/e 14835-14844, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.1c07067

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

Autori: Grossmann, Oleg., Maji, Rajat., Aukland, Miles. H., Lee, Sunggi., List, Benjamin
Pubblicato in: Angewandte Chemie International Edition, 2021, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202115036

Azine Activation via Silylium Catalysis

Autori: Obradors Carla, Benjamin List
Pubblicato in: Journal of the American Chemical Society, Numero 143(18), 2021, Pagina/e 6817-6822, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.1c03257

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

Autori: Das, S., Mitschke, Benjamin., De, C. K., Harden, I., Bistoni, G.,List, Benjamin
Pubblicato in: Nature Catalysis, Numero 4(12), 2021, Pagina/e 1043-1049, ISSN 2520-1158
Editore: New York : Nature Publishing Group
DOI: 10.1038/s41929-021-00714-x

Confinement as a Unifying Element in Selective Catalysis

Autori: Benjamin Mitschke, Mathias Turberg and Benjamin List
Pubblicato in: Chem, Numero 6(10), 2020, Pagina/e 2515-2532, ISSN 2451-9294
Editore: Elservier
DOI: 10.1016/j.chempr.2020.09.007

Catalytic Asymmetric Synthesis of Unprotected β 2 -Amino Acids

Autori: Chendan Zhu, Francesca Mandrelli, Hui Zhou, Rajat Maji, Benjamin List
Pubblicato in: Journal of the American Chemical Society, Numero 143/9, 2021, Pagina/e 3312-3317, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.1c00249

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

Autori: Hui Zhou, Pinglu Zhang, Benjamin List
Pubblicato in: Synlett 2022; 33(01): 38-39, Numero 33(01), 2021, Pagina/e 38-39, ISSN 0936-5214
Editore: Georg Thieme Verlag
DOI: 10.1055/a-1670-5829

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

Autori: Tynchtyk Amatov, Nobuya Tsuji, Rajat Maji, Lucas Schreyer, Hui Zhou, Markus Leutzsch, and Benjamin List
Pubblicato in: Journal of the American Chemical Society, Numero 143 (36), 2021, Pagina/e 14475-14481, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.1c07447

Organocatalytic stereoselective cyanosilylation of small ketones

Autori: Hui Zhou, Yu Zhou, Han Yong Bae, Markus Leutzsch, Yihang Li, Chandra Kanta De, Gui-Juan Cheng & Benjamin List1
Pubblicato in: Nature, Numero 605, 2022, Pagina/e 84 - 89, ISSN 2520-1158
Editore: 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

Autori: Ghosh, S., Erchinger, J. E., Maji, R., List, B.
Pubblicato in: Journal of the American Chemical Society, Numero 144 (15), 2022, Pagina/e 6703 - 6708, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.2c01971

The Smelling Principle of Vetiver Oil, Unveiled by Chemical Synthesis

Autori: Jie Ouyang, Hanyong Bae, Samuel Jordi, Quang Minh Dao, Sandro Dossenbach, Stefanie Dehn, Julia B. Lingnau, Chandra Kanta De, Philip Kraft, Benjamin List
Pubblicato in: Angewandte Chemie International Edition, Numero 60/11, 2021, Pagina/e 5666-5672, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202014609

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

Autori: Youwei Xie, Benjamin List
Pubblicato in: Angewandte Chemie International Edition, Numero 56/18, 2017, Pagina/e 4936-4940, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201612149

High Lithium Transference Number Electrolytes Containing Tetratriflylpropene’s Lithium Salt

Autori: J. Popovic, D. Höfler, J. P. Melchior, A. Münchinger, B. List, J. Maier
Pubblicato in: The Journal of Physical Chemistry Letters, Numero 9/17, 2018, Pagina/e 5116-5120, ISSN 1948-7185
Editore: 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

Autori: Han Yong Bae, Denis Höfler, Philip S. J. Kaib, Pinar Kasaplar, Chandra Kanta De, Arno Döhring, Sunggi Lee, Karl Kaupmees, Ivo Leito, Benjamin List
Pubblicato in: Nature Chemistry, Numero 10/8, 2018, Pagina/e 888-894, ISSN 1755-4330
Editore: Nature Publishing Group
DOI: 10.1038/s41557-018-0065-0

A Dendralenic C–H Acid

Autori: Denis Höfler, Richard Goddard, Nils Nöthling, Benjamin List
Pubblicato in: Synlett, Numero 30/04, 2019, Pagina/e 433-436, ISSN 0936-5214
Editore: 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

Autori: Han Yong Bae, Benjamin List
Pubblicato in: Chemistry - A European Journal, Numero 24/52, 2018, Pagina/e 13767-13772, ISSN 0947-6539
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/chem.201803142

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

Autori: Hyejin Kim, Gabriela Gerosa, Jonas Aronow, Pinar Kasaplar, Jie Ouyang, Julia B. Lingnau, Paul Guerry, Christophe Farès, Benjamin List
Pubblicato in: Nature Communications, Numero 10/1, 2019, Pagina/e 770, ISSN 2041-1723
Editore: 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

Autori: Tim Gatzenmeier, Mathias Turberg, Diana Yepes, Youwei Xie, Frank Neese, Giovanni Bistoni, Benjamin List
Pubblicato in: Journal of the American Chemical Society, Numero 140/40, 2018, Pagina/e 12671-12676, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.8b07092

Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates

Autori: Lucas Schreyer, Philip S. J. Kaib, Vijay N. Wakchaure, Carla Obradors, Roberta Properzi, Sunggi Lee, Benjamin List
Pubblicato in: Science, Numero 362/6411, 2018, Pagina/e 216-219, ISSN 0036-8075
Editore: 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

Autori: Jie Ouyang, Jennifer L. Kennemur, Chandra Kanta De, Christophe Farès, Benjamin List
Pubblicato in: Journal of the American Chemical Society, Numero 141/8, 2019, Pagina/e 3414-3418, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.8b13899

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

Autori: Sunggi Lee, Han Yong Bae, Benjamin List
Pubblicato in: Angewandte Chemie International Edition, Numero 57/37, 2018, Pagina/e 12162-12166, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201806312

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

Autori: Benjamin List, Chandra De, Raja Mitra
Pubblicato in: Synlett, Numero 28/18, 2017, Pagina/e 2435-2438, ISSN 0936-5214
Editore: Georg Thieme Verlag
DOI: 10.1055/s-0036-1590903

Activation of olefins via asymmetric Brønsted acid catalysis

Autori: Nobuya Tsuji, Jennifer L. Kennemur, Thomas Buyck, Sunggi Lee, Sébastien Prévost, Philip S. J. Kaib, Dmytro Bykov, Christophe Farès, Benjamin List
Pubblicato in: Science, Numero 359/6383, 2018, Pagina/e 1501-1505, ISSN 0036-8075
Editore: American Association for the Advancement of Science
DOI: 10.1126/science.aaq0445

A Purely Organic Tricarbanion

Autori: Denis Höfler, Richard Goddard, Julia B. Lingnau, Nils Nöthling, Benjamin List
Pubblicato in: Angewandte Chemie International Edition, Numero 57/27, 2018, Pagina/e 8326-8329, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201803647

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

Autori: Benjamin List, Sunggi Lee, Philip Kaib
Pubblicato in: Synlett, Numero 28/12, 2017, Pagina/e 1478-1480, ISSN 0936-5214
Editore: 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

Autori: Denis Höfler, Manuel van Gemmeren, Petra Wedemann, Karl Kaupmees, Ivo Leito, Markus Leutzsch, Julia B. Lingnau, Benjamin List
Pubblicato in: Angewandte Chemie International Edition, Numero 56/5, 2017, Pagina/e 1411-1415, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201609923

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

Autori: Sayantani Das, Nilanjana Majumdar, Chandra Kanta De, Dipti Sankar Kundu, Arno Döhring, Anika Garczynski, Benjamin List
Pubblicato in: Journal of the American Chemical Society, Numero 139/4, 2017, Pagina/e 1357-1359, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.6b12176

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

Autori: Tim Gatzenmeier, Philip S. J. Kaib, Julia B. Lingnau, Richard Goddard, Benjamin List
Pubblicato in: Angewandte Chemie International Edition, Numero 57/9, 2018, Pagina/e 2464-2468, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201712088

Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions

Autori: Sunggi Lee, Philip S. J. Kaib, Benjamin List
Pubblicato in: Journal of the American Chemical Society, Numero 139/6, 2017, Pagina/e 2156-2159, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.6b11993

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

Autori: Luping Liu, Hyejin Kim, Youwei Xie, Christophe Farès, Philip S. J. Kaib, Richard Goddard, Benjamin List
Pubblicato in: Journal of the American Chemical Society, Numero 139/39, 2017, Pagina/e 13656-13659, ISSN 0002-7863
Editore: 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

Autori: Francesca Mandrelli, Aurélie Blond, Thomas James, Hyejin Kim, Benjamin List
Pubblicato in: Angewandte Chemie International Edition, Numero 58/33, 2019, Pagina/e 11479-11482, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201905623

IDPi Catalysis

Autori: Schreyer Lucas, Properzi Roberta, List Benjamin
Pubblicato in: Angewandte Chemie International Edition, Numero 58(37), 2019, Pagina/e 12761-12777, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201900932

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

Autori: Pinglu Zhang, Nobuya Tsuji, Jie Ouyang, Benjamin List
Pubblicato in: Journal of the American Chemical Society, Numero 143/2, 2021, Pagina/e 675-680, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.0c12042

The Catalytic Asymmetric Intermolecular Prins Reaction

Autori: Díaz-Oviedo, C. David., Maji, Rajat.,List, Benjamin
Pubblicato in: J. Am. Chem. Soc. 2021, 143, 49, 20598, Numero 143(49), 2021, Pagina/e 20598-20604, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.1c10245

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

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

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

Autori: Ouyang, J., Maji, R., Leutzsch, M., Mitschke, B., & List, B.
Pubblicato in: Journal of the American Chemical Society, Numero 144 (19), 2022, Pagina/e 8460 - 8466, ISSN 0002-7863
Editore: American Chemical Society
DOI: 10.1021/jacs.2c02216

A Chiral, Dendralenic C–H Acid

Autori: Höfler, Dennis., & List, Benjamin
Pubblicato in: Synlett 2022; 33(01): 38-39, Numero 33(01), 2021, Pagina/e 38-39, ISSN 0936-5214
Editore: 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

Autori: Hui Zhou, Han Yong Bae, Markus Leutzsch, Jennifer L. Kennemur, Diane Bécart, Benjamin List
Pubblicato in: Journal of the American Chemical Society, Numero 142/32, 2020, Pagina/e 13695-13700, ISSN 0002-7863
Editore: 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

Autori: Santanu Ghosh, Sayantani Das, Chandra Kanta De, Diana Yepes, Frank Neese, Giovanni Bistoni, Markus Leutzsch, Benjamin List
Pubblicato in: Angewandte Chemie International Edition, Numero 59/30, 2020, Pagina/e 12347-12351, ISSN 1433-7851
Editore: John Wiley & Sons Ltd.
DOI: 10.1002/anie.202000307

Catalytic enantiocontrol over a non-classical carbocation

Autori: Roberta Properzi, Philip S. J. Kaib, Markus Leutzsch, Gabriele Pupo, Raja Mitra, Chandra Kanta De, Lijuan Song, Peter R. Schreiner and Benjamin List*
Pubblicato in: Nature Chemistry, Numero 12, 2020, Pagina/e 1174-1179, ISSN 1755-4330
Editore: Nature Publishing Group
DOI: 10.1038/s41557-020-00558-1