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SHUTTLE – Hydride Shuttle Catalysis

SHUTTLE – Hydride Shuttle Catalysis

Nuno Maulide (ORCID: 0000-0003-3643-0718)
  • Grant DOI 10.55776/P37182
  • Funding program Principal Investigator Projects
  • Status ongoing
  • Start March 1, 2024
  • End February 29, 2028
  • Funding amount € 399,346
  • Project website

Disciplines

Chemistry (100%)

Keywords

    Hydride Shuttle, Alkaloids, Synthetic Methods, Redox Isomerisation, Multicomponent Reactions

Abstract

While the funcon of chemical structures is not inherently based on their complexity, with many successful pharmaceucals being rather simple compounds, more elaborate structures hold much promise. Parcularly, oen even slight alteraons to chemical structure can elicit profound changes in biological acvity. Among such compounds, those containing nitrogen atoms within a cyclic structure are parcularly interesng and the development of more ecient syntheses remains of the highest importance. Drawing on the foundaon laid by previous work developed in our group, we propose the development of a range of new reacons, which are based on a concept termed inverse hydride shutle catalysis. This concept underpins a spectrum of novel reacons designed to yield a diverse array of products. Yet, while potenally giving access of a wide variety of dierent products, our proposed reacons can be comprehensively categorised as i) taking advantage of the rapid aggregaon of simple, and oen commercially available, starng materials, ii) employing metal-free catalysts for the selecve modicaon of nitrogen-containing structures and iii) delivering (poly)cyclic compounds with high complexity. Although the foundaonal principles of this concept have been elucidated in earlier work, our proposed endeavours aim to extend and generalize this process. Integraon with other reacons is pivotal, promising the generaon of heavily funconalized products with versale applicaons across various elds. The envisioned outcome is a streamlined and versale methodology that capitalizes on the "inverse hydride shutle catalysis" framework, and will give rise to much more heavily funconalised products with potenal applicaons in a wide variety of elds. This research project aspires to posion "inverse hydride shutle catalysis" as a universally applicable method, oering researchers across natural sciences and beyond a tool for the rapid synthesis of structures that were once beyond reach. The prospect of facilitang the exploraon of uncharted chemical territories underscores the broader impact of this methodology, transcending disciplinary boundaries and contribung to the advancement of scienc knowledge.

Research institution(s)
  • Universität Wien - 100%

Research Output

  • 61 Citations
  • 25 Publications
Publications
  • 2024
    Title Deprotective Lossen rearrangement: a direct and general transformation of Nms-amides to unsymmetrical ureas
    DOI 10.1039/d4sc04974h
    Type Journal Article
    Author Spieß P
    Journal Chemical Science
    Pages 15799-15803
    Link Publication
  • 2024
    Title Diastereoselective hydride transfer enables a synthesis of chiral 1,5-carboxamido-trifluoromethylcarbinols
    DOI 10.1039/d4sc05049e
    Type Journal Article
    Author Tinelli R
    Journal Chemical Science
    Pages 15751-15756
    Link Publication
  • 2024
    Title Hydride Shuttle Catalysis: From Conventional to Inverse Mode
    DOI 10.1021/jacsau.4c00532
    Type Journal Article
    Author Saridakis I
    Journal JACS Au
    Pages 3358-3369
    Link Publication
  • 2024
    Title Mechanistic differences between linear vs. spirocyclic dialkyldiazirine probes for photoaffinity labeling
    DOI 10.1039/d4sc04238g
    Type Journal Article
    Author O'Brien J
    Journal Chemical Science
    Pages 15463-15473
    Link Publication
  • 2024
    Title Stereocontrolled Synthesis of 1,4-Dicarbonyls via [3,3]-Sulfonium Rearrangement and Application to the Synthesis of Heterocycles
    DOI 10.1055/a-2446-3455
    Type Journal Article
    Author G.-Simonian N
    Journal Synlett
    Pages 759-764
  • 2024
    Title Asymmetrische Synthese von ß-Ketoamiden durch eine Sulfoniumumlagerung
    DOI 10.1002/ange.202418070
    Type Journal Article
    Author Porte V
    Journal Angewandte Chemie
    Link Publication
  • 2024
    Title Asymmetric Synthesis of ß-Ketoamides by Sulfonium Rearrangement
    DOI 10.1002/anie.202418070
    Type Journal Article
    Author Porte V
    Journal Angewandte Chemie International Edition
    Link Publication
  • 2024
    Title Revisiting the Baddeley Reaction: Access to Functionalized Decalins by Charge-Promoted Alkane Functionalization
    DOI 10.1002/anie.202418067
    Type Journal Article
    Author Vavrík M
    Journal Angewandte Chemie International Edition
    Link Publication
  • 2024
    Title Erneute Untersuchung der Baddeley Reaktion: Zugang zu funktionalisierten Decalinen durch ladungsinduzierte Alkanfunktionalisierung
    DOI 10.1002/ange.202418067
    Type Journal Article
    Author Vavrík M
    Journal Angewandte Chemie
    Link Publication
  • 2024
    Title Deprotective Functionalization: A Direct Conversion of Nms-Amides to Carboxamides Using Carboxylic Acids
    DOI 10.1002/anie.202318304
    Type Journal Article
    Author Spieß P
    Journal Angewandte Chemie International Edition
    Link Publication
  • 2024
    Title Entschützende Funktionalisierung: eine direkte Umwandlung von Nms-Amiden in Carbonsäureamide
    DOI 10.1002/ange.202318304
    Type Journal Article
    Author Spieß P
    Journal Angewandte Chemie
    Link Publication
  • 2024
    Title Stereodivergent Synthesis of 1,4-Dicarbonyl Compounds through Sulfonium Rearrangement: Mechanistic Investigation, Stereocontrolled Access to ?-Lactones and ?-Lactams, and Total Synthesis of Paraconic Acids
    DOI 10.1021/jacs.4c01755
    Type Journal Article
    Author G.-Simonian N
    Journal Journal of the American Chemical Society
    Pages 13914-13923
    Link Publication
  • 2024
    Title Lewis Säure-Getriebene Inverse Hydrid-Shuttle Katalyse
    DOI 10.1002/ange.202320001
    Type Journal Article
    Author Jones B
    Journal Angewandte Chemie
    Link Publication
  • 2024
    Title Lewis Acid-Driven Inverse Hydride Shuttle Catalysis
    DOI 10.1002/anie.202320001
    Type Journal Article
    Author Jones B
    Journal Angewandte Chemie International Edition
    Link Publication
  • 2024
    Title Domino Conjugate Addition-1,4-Aryl Migration for the Synthesis of a,ß-Difunctionalized Amides
    DOI 10.1021/jacsau.4c00378
    Type Journal Article
    Author Zhang H
    Journal JACS Au
    Pages 2456-2461
    Link Publication
  • 2024
    Title Iodide Anion Enables a Reductive Cross-Electrophile Coupling for Preparing Tertiary Amines
    DOI 10.1002/anie.202409688
    Type Journal Article
    Author Lemmerer M
    Journal Angewandte Chemie International Edition
    Link Publication
  • 2025
    Title Charge Relocation Enables a Modular and Diastereoselective Synthesis of cis-Substituted Tetrahydrofurans
    DOI 10.1002/anie.202503750
    Type Journal Article
    Author Niu Z
    Journal Angewandte Chemie International Edition
    Link Publication
  • 2025
    Title Facile (Z)-Selective Synthesis of ß,?-Unsaturated Ketones by a Silicon-based Olefination Strategy
    DOI 10.1002/anie.202517069
    Type Journal Article
    Author Aynetdinova D
    Journal Angewandte Chemie International Edition
    Link Publication
  • 2025
    Title Deprotective Functionalization: An Emerging Concept for Amine Reactivity
    DOI 10.1002/chem.202503271
    Type Journal Article
    Author Tiefenbrunner I
    Journal Chemistry – A European Journal
  • 2025
    Title Synthesis of Sterically Congested Carbonyl Compounds via an ipso-Selective Sulfonium Rearrangement
    DOI 10.1021/jacs.5c13777
    Type Journal Article
    Author Klose I
    Journal Journal of the American Chemical Society
    Pages 37899-37906
    Link Publication
  • 2025
    Title Regioselective Synthesis of ß,?-Unsaturated Amides from Unactivated Alkenes
    DOI 10.1021/acs.joc.5c00093
    Type Journal Article
    Author Vega-Ces S
    Journal The Journal of Organic Chemistry
    Pages 4121-4126
    Link Publication
  • 2025
    Title Diastereoselective Umpolung cyclisation of ketones promoted by hypervalent iodine
    DOI 10.1039/d5sc01085c
    Type Journal Article
    Author Iannelli G
    Journal Chemical Science
    Pages 10944-10950
    Link Publication
  • 2025
    Title Cationic, Iodine(III)-Mediated and Directed Diastereoselective Oxidation of Inert C-H Bonds in Cyclic Hydrocarbons
    DOI 10.1002/anie.202421872
    Type Journal Article
    Author G.-Simonian N
    Journal Angewandte Chemie International Edition
    Link Publication
  • 2025
    Title Kationische, Iod(III)-vermittelte und dirigierte diastereoselektive Oxidation inerter C-H-Bindungen in cyclischen Kohlenwasserstoffen
    DOI 10.1002/ange.202421872
    Type Journal Article
    Author G.-Simonian N
    Journal Angewandte Chemie
    Link Publication
  • 2024
    Title Iodid-Anion ermöglicht eine reduktive Kreuz-Elektrophil-Kupplung zur Herstellung tertiärer Amine
    DOI 10.1002/ange.202409688
    Type Journal Article
    Author Lemmerer M
    Journal Angewandte Chemie
    Link Publication

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