Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 26, Pages 10279-10282Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo701959b
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[GRAPHICS] The use of L-proline (30 mol %) and MW irradiation (13 W) with cooling promotes in a few hours the almost quantitative anomerization of alpha-C-glycosylmethyl aldehydes into beta-isomers. An open-chain enamine-based mechanism is postulated for this transformation. The anomerization of alpha-ketones was instead achieved by the pyrrolidine/TFA couple and MW irradiation at 120 degrees C (enamine mechanism) and by DBU as Bronsted base (enolate mechanism).
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