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Hydride shift generated oxonium ions: evidence for mechanism and intramolecular trapping experiments to form trans THF derivatives.

Abstract:
(Chemical Equation Presented) Switching sides: cis THF derivatives produced from the oxidative cyclization of dienes and diols can be transformed into the corresponding trans heterocycles through a 1,2-hydride shift and intramolecular trapping with a hydride nucleophile (see scheme). Moreover, organometallic compounds can be used to trap the oxonium ion generated in this way so that it is possible to introduce various groups at the C-2 position with control of stereochemistry. © 2008 Wiley-VCH Verlag GmbH and Co. KGaA.
Publication status:
Published

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Publisher copy:
10.1002/anie.200705340

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Williams, O More by this author
Churchill, GH More by this author
Journal:
Angewandte Chemie (International ed. in English)
Volume:
47
Issue:
15
Pages:
2869-2871
Publication date:
2008
DOI:
EISSN:
1521-3773
ISSN:
1433-7851
URN:
uuid:96bcb218-b79a-4985-b608-3bfe37ebb14a
Source identifiers:
34150
Local pid:
pubs:34150

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