On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet

Freda K. Chio; Julie Warne; Damien Gough; Mark Penny; Sasa Green (née Martinović); Simon J. Coles; Mike B. Hursthouse; Peter Jones; Lorraine Hassall; Thomas M. McGuire; Adrian P. Dobbs

doi:10.1016/j.tet.2011.05.019

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On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet

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On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet

Freda K. Chio, Julie Warne, Damien Gough, Mark Penny, Sasa Green (née Martinović), Simon J. Coles, Mike B. Hursthouse, Peter Jones, Lorraine Hassall, Thomas M. McGuire, …

Tetrahedron, Vol.67(27), pp.5107-5124

08/07/2011

DOI: https://doi.org/10.1016/j.tet.2011.05.019

Abstract

Civet

Dihydropyran

Fluorinated pyran

Lewis acid

Mukaiyama–Aldol–silyl-Prins reaction

Prins reaction

Pyran

Silyl-Prins reaction

While developing new variations of the Prins cyclisation reaction, the effect of the choice of Lewis acid on the outcome of the reaction and the product(s) has been investigated, yielding hitherto unseen dihydropyran products in the Prins cyclisation reaction of homoallylic alcohols, and two new modifications of the reaction: the triflate-trapped Prins adduct and the Mukaiyama–Aldol–silyl-Prins reaction. Two of these methods are employed in two complementary total syntheses of the important perfumery compound, (±)-Civet. [Display omitted]

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Title: On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet
Creators: Freda K. Chio - Queen Mary University of London
Julie Warne - Queen Mary University of London
Damien Gough - Queen Mary University of London
Mark Penny - Queen Mary University of London
Sasa Green (née Martinović) - University of Exeter
Simon J. Coles - University of Southampton
Mike B. Hursthouse - University of Southampton
Peter Jones - Pfizer
Lorraine Hassall - AstraZeneca
Thomas M. McGuire - AstraZeneca
Adrian P. Dobbs - Queen Mary University of London
Publication Details: Tetrahedron, Vol.67(27), pp.5107-5124
Publisher: Elsevier Ltd
Number of pages: 18
Publication Date: 08/07/2011
Identifiers: 99959866902346; WOS:000292721000016
Academic Unit: School of Chemistry and Chemical Engineering; Department of Chemistry
Language: English
Resource Type: Journal article

On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet

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