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Stereoselective synthesis of bicyclo[3.n.1]alkenone frameworks by Lewis acid-catalysis
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-6536-8506
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-9085-0476
2017 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 53, no 82, p. 11353-11356Article in journal (Refereed) Published
Abstract [en]

An intermolecular cyclization of alkynyl enones with cyclic ketones for the synthesis of bicyclo[3.n.1]alkenones is reported. This protocol exhibits a high functional group tolerance and provides access to a variety of bicyclic systems found as skeletons in many natural products.

Place, publisher, year, edition, pages
2017. Vol. 53, no 82, p. 11353-11356
National Category
Chemical Sciences
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-148991DOI: 10.1039/c7cc06400dISI: 000412814900017PubMedID: 28967928OAI: oai:DiVA.org:su-148991DiVA, id: diva2:1160815
Available from: 2017-11-28 Created: 2017-11-28 Last updated: 2018-02-20Bibliographically approved
In thesis
1. Development of new Catalytic Methods for the Selective Synthesis of Heterocycles
Open this publication in new window or tab >>Development of new Catalytic Methods for the Selective Synthesis of Heterocycles
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In the field of organic chemistry, the development of new catalytic methods for the synthesis of complex molecules from simple precursors is a top priority. The main focus of this thesis concerns the diastereoselective synthesis of heterocyclic compounds using main group elements as Lewis acid catalysts.

The first part of this thesis deals with an annulation reaction of nitrones with oxiranes, aziridines, and thiiranes using Al(III) or In(III) catalysts. From this protocol, 1,4,2-dioxazinanes, 1,2,4-oxadiazinanes, and 1,4,2-oxathiazinanes were obtained in moderate to high yields with excellent diastereoselectivity. The transformation was found to be stereospecific and proceed via an SN2-mechanism.

The second and third parts concern the development of In(III)-catalyzed annulation of carbonyl compounds, amines, and alkynyl enones. InBr3 was found to be an efficient catalyst for the activation of alkynyl enones in a multicomponent reaction with aldehydes and amines. The method affords cyclopenta[c]furans in high yields and in good to excellent diastereomeric ratios. Bicyclo[3.n.1]alkenone derivatives were formed via a double Michael addition reaction of cyclic ketones, amines, and alkynyl enones, in the presence of InCl3. The utility of these protocols was also demonstrated by sequential transformations.

In the fourth part, AgOTf and CuI were found to be efficient catalysts for the activation of pyridine-substituted enynes towards enamines, providing indolizine derivatives in high yield and good diastereomeric ratios.

In the last part of the thesis, 1,2-aminoarylation of γ,δ-unsaturated oxime esters with arylboronic acids using Ni catalysis is discussed. The protocol demonstrates the potential of Ni-catalysts for the generation of iminyl radicals to furnish functionalized pyrroline derivatives. The utility of this protocol was exemplified by transforming the pyrroline products to the corresponding pyrrole and pyrrolidine derivatives. 

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2018. p. 65
Keyword
catalysis, indium, heterocycles, Lewis acid, multicomponent reactions, furans, alkynes
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-153088 (URN)978-91-7797-093-4 (ISBN)978-91-7797-094-1 (ISBN)
Public defence
2018-04-06, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 4: Manuscript.

Available from: 2018-03-14 Created: 2018-02-20 Last updated: 2018-03-19Bibliographically approved

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Pathipati, Stalin R.Eriksson, LarsSelander, Nicklas
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