Stereoelectronic control of the base-catalysed rearrangement of 2-hydroxy-3-oxocarboxylates
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- Vol. 22 (3) , 381-385
- https://doi.org/10.1039/p29910000381
Abstract
The stereochemistry of the alkali-catalysed rearrangement of α-acetohydroxybutyrate (2-ethyl-2-hydroxy-3-oxobutanoate) was studied. The rearrangement was found to proceed via a transition state in which a syn arrangement of the C–O bonds is preferred over the anti arrangement by a factor of ≥2:1.Keywords
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