SHUTTLE – Hydride Shuttle Catalysis
SHUTTLE – Hydride Shuttle Catalysis
Disciplines
Chemistry (100%)
Keywords
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Hydride Shuttle,
Alkaloids,
Synthetic Methods,
Redox Isomerisation,
Multicomponent Reactions
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.
- Universität Wien - 100%
Research Output
- 61 Citations
- 25 Publications
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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 VavrÃk 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 VavrÃk 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