An unexpected Prins desymmetrisation reaction driven by silyl migration

Butters, Michael, Elliott, Mark Christopher ORCID: https://orcid.org/0000-0003-0132-0818 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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Abstract

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:	06 May 2023 05:37
URI:	https://orca.cardiff.ac.uk/id/eprint/39846

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