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

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

Chio, Freda K., Warne, Julie, Gough, Damien, Penny, Mark, Green, Sasa, Coles, Simon J., Hursthouse, Mike B., Jones, Peter, Hassall, Lorraine, McGuire, Thomas M. and Dobbs, Adrian P. (2011) On the choice of Lewis acids for the Prins reaction; two total syntheses of (±)-Civet. Tetrahedron, 67 (27-28). pp. 5107-5124. ISSN 0040-4020 (doi:10.1016/j.tet.2011.05.019)

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: Prins reaction, silyl-Prins reaction, MukaiyamaeAldolesilyl-Prins reaction, Pyran, Dihydropyran, fluorinated pyran, Lewis acid, Civet
Subjects: Q Science > QD Chemistry
Faculty / Department / Research Group: Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
Related URLs:
Last Modified: 17 Oct 2016 09:12
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/9981

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