Asymmetric a-Functionalization of Carboxylic Acids/Esters
Asymmetric a-Functionalization of Carboxylic Acids/Esters
Disciplines
Chemistry (100%)
Keywords
-
Heterofunctionalizations,
Asymmetric Organocatalysis,
Carbofunctionalizations,
Ammonium Enolates,
Carboxylic Acid Derivatives
The direct -functionalization of simple acyclic carboxylic acid derivatives is a challenging task and this project aims on the development of new strategies to carry out such reactions in an asymmetric fashion. We will hereby rely on the use of chiral Lewis base catalysts which provide a highly reactive chiral ammonium enolate intermediate upon reaction with simple starting materials. This intermediate will then undergo the targeted asymmetric -hetero- and carbofunctionalization reactions. The hereby accessed enantioenriched products are of high value for further applications and therefore this project will provide powerful tools to overcome challenging synthesis problem and will give access to a variety of interesting chiral small molecules in a so far unprecedented and highly efficient manner relying on simple starting materials.
- Universität Linz - 100%
Research Output
- 210 Citations
- 21 Publications
-
2020
Title Recent Progress in the Asymmetric Syntheses of a-Heterofunctionalized (Masked) a- and ß-Amino Acid Derivatives DOI 10.1002/ejoc.202001077 Type Journal Article Author Eder I Journal European Journal of Organic Chemistry Pages 202-219 Link Publication -
2022
Title Recent Developments and Trends in Asymmetric Organocatalysis DOI 10.1002/ejoc.202200950 Type Journal Article Author Mancheño O Journal European Journal of Organic Chemistry Link Publication -
2022
Title Enantioselective organocatalytic syntheses of a-selenated a- and ß-amino acid derivatives DOI 10.1039/d1ob02235k Type Journal Article Author Haider V Journal Organic & Biomolecular Chemistry Pages 824-830 Link Publication -
2024
Title Enantioselective a-heterofunctionalization reactions of catalytically generated C1-Lewis base enolates DOI 10.1016/j.tchem.2024.100063 Type Journal Article Author Piringer M Journal Tetrahedron Chem Pages 100063 Link Publication -
2024
Title Chiral Lewis Bases for Asymmetric Organocatalysis DOI 10.52843/cassyni.t7mdbs Author Waser M Link Publication -
2023
Title Chiral Lewis Base-Catalysed Asymmetric Syntheses of Benzo-fused ?-Lactones DOI 10.1002/ejoc.202300704 Type Journal Article Author Stockhammer L Journal European Journal of Organic Chemistry Link Publication -
2023
Title Cooperative Chiral Lewis Base/Palladium-Catalyzed Asymmetric Syntheses of Methylene-Containing d-Lactams DOI 10.1002/ejoc.202300982 Type Journal Article Author Zebrowski P Journal European Journal of Organic Chemistry Link Publication -
2020
Title Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric a-Hydroxylation of ß-Ketoesters DOI 10.1021/acs.orglett.0c02198 Type Journal Article Author Mairhofer C Journal Organic Letters Pages 6138-6142 Link Publication -
2020
Title Asymmetric a-Chlorination of ß-Keto Esters Using Hypervalent Iodine-Based Cl-Transfer Reagents in Combination with Cinchona Alkaloid Catalysts DOI 10.1002/ejoc.202001217 Type Journal Article Author Stockhammer L Journal European Journal of Organic Chemistry Pages 82-86 Link Publication -
2022
Title Stereoselective Syntheses of Masked ß-Amino Acid Containing Phthalides DOI 10.1002/hlca.202200110 Type Journal Article Author Serusi L Journal Helvetica Chimica Acta Link Publication -
2022
Title Enantioselective ß-Selective Addition of Isoxazolidin-5-ones to Allenoates Catalyzed by Quaternary Ammonium Salts DOI 10.1055/a-1948-5493 Type Journal Article Author Zebrowski P Journal Synthesis Pages 1706-1713 Link Publication -
2023
Title Isothiourea-Catalyzed Enantioselective Functionalisation of Glycine Schiff Base Aryl Esters via 1,6- and 1,4-Additions DOI 10.1002/ceur.202300015 Type Journal Article Author Stockhammer L Journal ChemistryEurope Link Publication -
2023
Title Photochemical Wolff Rearrangement Initiated Generation and Subsequent a-Chlorination of C1 Ammonium Enolates DOI 10.1021/acs.orglett.3c00986 Type Journal Article Author Weinzierl D Journal Organic Letters Pages 3126-3130 Link Publication -
2021
Title Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF3S-, 3-RS-, and 3-F-Substituted Isoindolinones DOI 10.1002/adsc.202100029 Type Journal Article Author Eitzinger A Journal Advanced Synthesis & Catalysis Pages 1955-1962 Link Publication -
2021
Title Enantiospecific deoxyfluorination of cyclic a-OH-ß-ketoesters DOI 10.1039/d0ob02152k Type Journal Article Author Mairhofer C Journal Organic & Biomolecular Chemistry Pages 162-165 Link Publication -
2021
Title Enantioselective a-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions DOI 10.1021/acs.orglett.1c02256 Type Journal Article Author Stockhammer L Journal Organic Letters Pages 6143-6147 Link Publication -
2021
Title Organocatalytic asymmetric a-functionalizations of ß-ketoesters with hypervalent iodine-based reagents and catalysts DOI 10.24820/ark.5550190.p011.612 Type Journal Article Author Mairhofer C Journal Arkivoc Pages 112-127 Link Publication -
2021
Title Chiral Isothiourea-Catalyzed Kinetic Resolution of 4-Hydroxy[2.2]paracyclophane DOI 10.3762/bxiv.2021.14.v1 Type Preprint Author Weinzierl D Pages 14 Link Publication -
2021
Title Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane DOI 10.3762/bjoc.17.68 Type Journal Article Author Weinzierl D Journal Beilstein Journal of Organic Chemistry Pages 800-804 Link Publication -
2021
Title Synthesis of [2.2]Paracyclophane-Based Glycidic Amides Using Chiral Ammonium Ylides DOI 10.1002/hlca.202100073 Type Journal Article Author Weinzierl D Journal Helvetica Chimica Acta Link Publication -
2021
Title Enantioselective Catalytic Synthesis of a-Halogenated a-Aryl-ß2,2-amino Acid Derivatives DOI 10.1021/acsorginorgau.1c00025 Type Journal Article Author Zebrowski P Journal ACS Organic & Inorganic Au Pages 34-43 Link Publication