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CHAOS SIGNED

C-H Acids for Organic Synthesis

Total Cost €

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EC-Contrib. €

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Partnership

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Project "CHAOS" data sheet

The following table provides information about the project.

Coordinator
MAX PLANCK INSTITUT FUER KOHLENFORSCHUNG 

Organization address
address: KAISER WILHELM PLATZ 1
city: MUELHEIM AN DER RUHR
postcode: 45470
website: www.kofo.mpg.de

contact info
title: n.a.
name: n.a.
surname: n.a.
function: n.a.
email: n.a.
telephone: n.a.
fax: n.a.

 Coordinator Country Germany [DE]
 Total cost 2˙007˙500 €
 EC max contribution 2˙007˙500 € (100%)
 Programme 1. H2020-EU.1.1. (EXCELLENT SCIENCE - European Research Council (ERC))
 Code Call ERC-2015-AdG
 Funding Scheme ERC-ADG
 Starting year 2016
 Duration (year-month-day) from 2016-10-01   to  2021-09-30

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    MAX PLANCK INSTITUT FUER KOHLENFORSCHUNG DE (MUELHEIM AN DER RUHR) coordinator 2˙007˙500.00

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 Project objective

Enantioselective Brønsted acid organocatalysis has the potential to revolutionize asymmetric synthesis. However, the commonly used chiral phosphoric acid catalysts are typically limited to certain, fairly reactive substrate classes such as imines. Recently, more active and stereoselective catalysts have been introduced, which rely on acidic N–H bonds, and which have significantly widened the scope of suitable substrates. Despite the considerable success of these catalysts, however, several important and highly attractive substrate classes still remain out of reach. The applicant’s group has now identified C–H acids as novel and highly promising candidates to tackle these long standing challenges. Here, a research program with three major goals is proposed: 1) broadly conceived synthetic studies will be undertaken, which are expected to give access to C–H acids with a wide range of acidity and steric confinement. 2) These C–H acids will be applied to address one of the most general limitations currently encountered in organocatalysis: The enantioselective conversion of small and unbiased substrates. 3) The developed C–H acids, which are expected to enable unprecedented acidities and catalytic activities, will be employed in the activation of increasingly less reactive electrophiles, for example aliphatic aldehydes but also esters and olefins, for which enantioselective organocatalytic reactions are currently very limited or even unknown. Overall, this research program will aim at the design, synthesis and application of C–H acids as platform for solving several long standing challenges in asymmetric organocatalysis. The introduction of C–H acids for organic synthesis is expected to enrich the toolbox of synthetic chemists in both academic and industrial laboratories.

 Publications

year authors and title journal last update
List of publications.
2019 Francesca Mandrelli, Aurélie Blond, Thomas James, Hyejin Kim, Benjamin List
Deracemizing α-Branched Carboxylic Acids by Catalytic Asymmetric Protonation of Bis-Silyl Ketene Acetals with Water or Methanol
published pages: 11479-11482, ISSN: 1433-7851, DOI: 10.1002/anie.201905623
Angewandte Chemie International Edition 58/33 2019-11-22
2017 Youwei Xie, Benjamin List
Catalytic Asymmetric Intramolecular [4+2] Cycloaddition of In Situ Generated ortho -Quinone Methides
published pages: 4936-4940, ISSN: 1433-7851, DOI: 10.1002/anie.201612149
Angewandte Chemie International Edition 56/18 2019-06-13
2019 Denis Höfler, Richard Goddard, Nils Nöthling, Benjamin List
A Dendralenic C–H Acid
published pages: 433-436, ISSN: 0936-5214, DOI: 10.1055/s-0037-1612246
Synlett 30/04 2019-06-06
2019 Hyejin Kim, Gabriela Gerosa, Jonas Aronow, Pinar Kasaplar, Jie Ouyang, Julia B. Lingnau, Paul Guerry, Christophe Farès, Benjamin List
A multi-substrate screening approach for the identification of a broadly applicable Diels–Alder catalyst
published pages: 770, ISSN: 2041-1723, DOI: 10.1038/s41467-019-08374-z
Nature Communications 10/1 2019-06-06
2019 Jie Ouyang, Jennifer L. Kennemur, Chandra Kanta De, Christophe Farès, Benjamin List
Strong and Confined Acids Enable a Catalytic Asymmetric Nazarov Cyclization of Simple Divinyl Ketones
published pages: 3414-3418, ISSN: 0002-7863, DOI: 10.1021/jacs.8b13899
Journal of the American Chemical Society 141/8 2019-06-06
2018 Sunggi Lee, Han Yong Bae, Benjamin List
Can a Ketone Be More Reactive than an Aldehyde? Catalytic Asymmetric Synthesis of Substituted Tetrahydrofurans
published pages: 12162-12166, ISSN: 1433-7851, DOI: 10.1002/anie.201806312
Angewandte Chemie International Edition 57/37 2019-06-06
2018 Tim Gatzenmeier, Mathias Turberg, Diana Yepes, Youwei Xie, Frank Neese, Giovanni Bistoni, Benjamin List
Scalable and Highly Diastereo- and Enantioselective Catalytic Diels–Alder Reaction of α,β-Unsaturated Methyl Esters
published pages: 12671-12676, ISSN: 0002-7863, DOI: 10.1021/jacs.8b07092
Journal of the American Chemical Society 140/40 2019-06-06
2018 Lucas Schreyer, Philip S. J. Kaib, Vijay N. Wakchaure, Carla Obradors, Roberta Properzi, Sunggi Lee, Benjamin List
Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates
published pages: 216-219, ISSN: 0036-8075, DOI: 10.1126/science.aau0817
Science 362/6411 2019-06-06
2018 Han Yong Bae, Denis Höfler, Philip S. J. Kaib, Pinar Kasaplar, Chandra Kanta De, Arno Döhring, Sunggi Lee, Karl Kaupmees, Ivo Leito, Benjamin List
Approaching sub-ppm-level asymmetric organocatalysis of a highly challenging and scalable carbon–carbon bond forming reaction
published pages: 888-894, ISSN: 1755-4330, DOI: 10.1038/s41557-018-0065-0
Nature Chemistry 10/8 2019-06-07
2018 J. Popovic, D. Höfler, J. P. Melchior, A. Münchinger, B. List, J. Maier
High Lithium Transference Number Electrolytes Containing Tetratriflylpropene’s Lithium Salt
published pages: 5116-5120, ISSN: 1948-7185, DOI: 10.1021/acs.jpclett.8b01846
The Journal of Physical Chemistry Letters 9/17 2019-06-06

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