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New routes to highly functionalised compounds from vinylcyclopropanes

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thesis
posted on 27.07.2018, 11:40 authored by Elisabeth J. Wyatt
Studies towards the development of a novel methodology have been achieved. A Palladium-catalysed [3 + 2] cycloaddition is described herein. Doubly activated vinylcyclopropanes have been ring opened with palladium (0) and the resulting zwitterionic π-allyl palladium species have participated in a nucleophilic addition with activated carbonyl moieties to construct tetrahydrofurans as a mixture of diastereoisomers. The palladium-catalysed [3 + 2] cycloaddition has shown to be successful with ketone moieties activated by an adjacent electron-withdrawing group such as ethyl esters in a range of α-keto esters, and amides in a range of substituted isatins (scheme 1). The reaction boasts good yields and the stereochemical preference of the reaction has shown to be dependent on the choice of reaction solvent. [Illustration omitted.] The reaction has shown to be successful on application to the intramolecular mode to form a bicyclic heterocycle (scheme 2). [Illustration omitted.] The methodology has been successfully incorporated towards the synthesis of the natural product monocerin.

History

School

  • Science

Department

  • Chemistry

Publisher

© Elisabeth Jane Wyatt

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2005

Notes

A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.

Language

en

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