Zvarec, O. and Avery, T.D. and Taylor, D.K. and Tiekink, E.R.T. (2010) Cyclisation of 1,2-dioxines containing tethered hydroxyl and carboxylic acid functionality: Synthesis of tetrahydrofurans and dihydrofuran-2(3H)-ones. Tetrahedron, 66 (4). pp. 1007-1013.
Full text not available from this repository.Abstract
Herein we outline cyclisations of tethered hydroxyl and carboxylic acid moieties onto the olefinic motif of 1,2-dioxines to generate tetrahydrofurans and dihydrofuran-2(3H)-ones, whilst maintaining the peroxide linkage intact. This work demonstrates the first examples of intramolecular cyclisation of tethered hydroxyl groupings onto 1,2-dioxines generating functionalised THFs in a highly stereoselective manner and includes improved methods for previously reported carboxylic acid tether cyclisations. Additionally, improved methods for the oxidation of 1,2-dioxines containing tethered alcohols to furnish tethered carboxylic acids are also detailed. Subsequent reduction of the peroxide linkage enables the generation of functionalised tetrahydrofurans and dihydrofuran-2(3H)-ones, which are useful building blocks for the construction of natural products. (C) 2009 Elsevier Ltd. All rights reserved.
| Item Type: | Article |
|---|---|
| Funders: | UNSPECIFIED |
| Uncontrolled Keywords: | 1,2-Dioxine; Tetrahydrofurans; Dihydrofuran-2(3H)-ones; Cyclisation |
| Subjects: | Q Science > Q Science (General) |
| Depositing User: | MR Faizal II H |
| Date Deposited: | 23 Dec 2015 03:15 |
| Last Modified: | 23 Dec 2015 03:15 |
| URI: | http://eprints.um.edu.my/id/eprint/15263 |
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