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An unexpected Prins desymmetrisation reaction driven by silyl migration

Butters, Michael, Elliott, Mark Christopher and Hill-Cousins, Joseph T. 2012. An unexpected Prins desymmetrisation reaction driven by silyl migration. Arkivoc Online Journal of Organic Chemistry 2012 (7) , pp. 113-125.

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Prins desymmetrisation reactions of cyclohexa-1,4-diene derivatives have been investigated as a route to the core of the cladiellin diterpenes. During the course of this work, we observed the formation of a partially-reduced benzofuran 18, which is clearly derived from oxocarbenium ion 21. This can only be rationalised by an unexpected primary to secondary silyl group migration.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: Prins reaction, tetrahydrofuran, heterocycle, diterpene, natural product
Publisher: Arkat USA Inc
ISSN: 1551-7004
Last Modified: 04 Jun 2017 04:29

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