Dokument: Enantioselective Allylation and Halocyclization of Allyl Hydrazides and Allyl Oximes for the Synthesis of Enantioenriched Pyrazolidines and Isoxazolidines
| Titel: | Enantioselective Allylation and Halocyclization of Allyl Hydrazides and Allyl Oximes for the Synthesis of Enantioenriched Pyrazolidines and Isoxazolidines | |||||||
| URL für Lesezeichen: | https://docserv.uni-duesseldorf.de/servlets/DocumentServlet?id=49694 | |||||||
| URN (NBN): | urn:nbn:de:hbz:061-20190531-104851-7 | |||||||
| Kollektion: | Dissertationen | |||||||
| Sprache: | Englisch | |||||||
| Dokumententyp: | Wissenschaftliche Abschlussarbeiten » Dissertation | |||||||
| Medientyp: | Text | |||||||
| Autor: | Reineke, Jana [Autor] | |||||||
| Dateien: |
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| Beitragende: | Prof. Dr. Constantin Czekelius [Gutachter] Priv. Doz.. Dr. Klaus Schaper [Gutachter] | |||||||
| Stichwörter: | Palladium-Katalyse, Halocyclisierung, enantioselektive Tsuji-Trost-Allylierung, Isoxazolidin, Pyrazolidin | |||||||
| Dewey Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik » 540 Chemie | |||||||
| Beschreibung: | N,N’-Diprotected hydrazides were synthesized and investigated as nucleophiles for monoallylation in a nucleophilic substitution reaction with (E)-cinnamyl bromide. The thus obtained monoallylated compounds were subjected to halocyclization conditions. trans-Ethyl 4-bromo-3-phenylpyrazolidine-1-carboxylate was obtained in 33% yield.
Diary ketoximes and symmetrically substituted allylic carbonates or acetates were synthesized and subjected to an asymmetric Tsuji-Trost reaction mediated by palladium-catalysis and the chiral hybrid ligand (R)-bis(3,5-dimethylphenyl)(2’-vinyl-[1,1’-binaphthalen]-2-yl)phosphane. The obtained allyl oximes were cyclized with bis(2,4,6-trimethylpyridine)bromine(I) hexafluorophosphate in a diastereoselective halocyclization reaction and the resulting isoxazolidines protected with benzoyl chloride. A “one-pot” protocol for this reaction sequence was developed. The N-protected trisubstituted isoxazolidines were obtained in overall yields of 38% to 69% for the three-step transformation and enantiomeric excesses up to 95%. | |||||||
| Lizenz: |  Urheberrechtsschutz | |||||||
| Bezug: | 11.2015 - 12.2018 | |||||||
| Fachbereich / Einrichtung: | Mathematisch- Naturwissenschaftliche Fakultät | |||||||
| Dokument erstellt am: | 31.05.2019 | |||||||
| Dateien geändert am: | 31.05.2019 | |||||||
| Promotionsantrag am: | 10.01.2019 | |||||||
| Datum der Promotion: | 29.03.2019 |
