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Construction of Tetrahydrofuran-3-ones from Readily Available Organochalcogen Precursors via Radical Carbonylation/Reductive Cyclization
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen, Avdelningen för organisk kemi.
2002 Ingår i: Organic Letters, Vol. 4, s. 3-Artikel i tidskrift (Refereegranskat) Published
Ort, förlag, år, upplaga, sidor
2002. Vol. 4, s. 3-
Identifikatorer
URN: urn:nbn:se:uu:diva-91438OAI: oai:DiVA.org:uu-91438DiVA, id: diva2:164162
Tillgänglig från: 2004-02-26 Skapad: 2004-02-26Bibliografiskt granskad
Ingår i avhandling
1. Synthesis of Tetrahydrofuran and Pyrrolidine Derivatives Utilising Radical Reactions: Organochalcogenides in Reductive, Carbonylative and Group-Transfer Cyclisation
Öppna denna publikation i ny flik eller fönster >>Synthesis of Tetrahydrofuran and Pyrrolidine Derivatives Utilising Radical Reactions: Organochalcogenides in Reductive, Carbonylative and Group-Transfer Cyclisation
2004 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

This thesis describes free-radical reactions for the construction of tetrahydrofuran and pyrrolidine derivatives. The studies are concerned with (i) diastereoselectivity in radical cyclisation, (ii) construction of tetrahydrofuran-3-ones and pyrrolidin-3-ones via radical carbonylation/cyclisation and (iii) synthesis of tetrahydrofuran derivatives via group-transfer cyclisation of organochalcogen compounds.

(i) Diastereoselectivity in the synthesis of tetrahydrofuran derivatives via radical cyclisation was controlled by addition of Lewis acids. In the synthesis of 2,4-disubstitued tetrahydrofurans, the trans-isomer was formed as the major product in the unperturbed reaction. Upon addition of trialkylalumiums the diastereoselectivity was reversed. In a similar fashion, exo/endo-diastereoselectivity in the synthesis of bicyclic 2,3,4-trisubstituted tetrahydrofurans could also be controlled.

(ii) Procedures for construction of tetrahydrofuran-3-ones and pyrrolidin-3-ones were presented. Epoxides were ring-opened with benzeneselenolate or benzenetellurolate and the resulting β-hydroxyalkyl phenyl chalcogenides were vinylated using ethyl propiolate/NMM or E-1,2-bis(phenylsulfonyl)ethylene/NaH. The corresponding nitrogen analogues were accessed by N-vinylation of aziridines followed by benzeneselenolate ring-opening. The two types of organochalcogen radical precursors were then treated with TTMSS/AIBN under an atmosphere of carbon monoxide (80 atm) to afford tetrahydrofuran-3-ones and pyrrolidin-3-ones, respectively, in high yields.

(iii) Microwaves were found to induce group-transfer cyclisation of β-allyloxyalkyl aryl chalcogenides. Short time heating (3-10 min) at 250 oC in ethylene glycol was required to obtain tetrahydrofuran derivatives in 60-91% yield.

Ort, förlag, år, upplaga, sidor
Uppsala: Acta Universitatis Upsaliensis, 2004. s. 46
Serie
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1104-232X ; 946
Nyckelord
Organic chemistry, Organisk kemi
Nationell ämneskategori
Organisk kemi
Identifikatorer
urn:nbn:se:uu:diva-4018 (URN)91-554-5893-9 (ISBN)
Disputation
2004-03-18, B42, BMC, Uppsala, 10:15
Opponent
Handledare
Tillgänglig från: 2004-02-26 Skapad: 2004-02-26Bibliografiskt granskad

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