Ausbruch aus der Ebene: Erkundung des Dreidimensionalen chemischen Strukturraums heterocyclischer Ringe - Diastereoselektive Rhodium-katalysierte Hydrierungen
Translated title:
Escape from Flatland: Exploring the Three-Dimensional Chemical Structure Space of Heterocyclic Rings - Diastereoselective Rhodium-Catalyzed Hydrogenation Reactions
Author:
Schiwek, Christian Herbert
Year:
2022
Document type:
Dissertation
Faculty/School:
TUM School of Natural Sciences
Advisor:
Bach, Thorsten (Prof. Dr.)
Referee:
Bach, Thorsten (Prof. Dr.); Köhler, Klaus (Prof. Dr.)
Language:
de
Subject group:
CHE Chemie
TUM classification:
CHE 600
Abstract:
Aliphatische N-Heterocyclen, wie Octahydroindolone oder aliphatische 2,5-Diketopiperazine (2,5-DKPs) gehören zu den begehrtesten Gerüsten in Naturstoffen, Pharmazeutika und Agrochemikalien. Wir berichten hier über die neuartige chemo- und diastereoselektive Arenhydrierung einer Reihe von N-Heterocyclen, darunter 2-Oxindole, 3,4-Dihydrochinolone sowie 2,5-DKPs und verwandte Strukturen. Diese Ergebnisse sind weitere Schritte zur Eroberung des dreidimensionalen chemischen Strukturraums.
Translated abstract:
Aliphatic N-heterocycles, like octahydroindolones or aliphatic 2,5-diketopiperazines (2,5-DKPs) are among the most coveted scaffolds in natural products, pharmaceuticals and agrochemicals. We herein reported the novel chemo- and diastereoselective arene hydrogenation of an array of N-heterocycles including 2-oxindoles, 3,4-dihydroquinolones as well as 2,5-DKPs and related structures. These advances are further steps to conquer the three dimensional chemical structure space.
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