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