Microwave-Assisted Organocatalytic Anomerization of α-C-Glycosylmethyl Aldehydes and Ketones.
- Resource Type
- Article
- Authors
- Massi, Alessandro; Nuzzi, Andrea; Dondoni, Alessandro
- Source
- Journal of Organic Chemistry. 12/21/2007, Vol. 72 Issue 26, p10279-10282. 4p. 1 Diagram, 4 Charts.
- Subject
- *PYRROLIDINE
*PROLINE
*ALDEHYDES
*ORGANIC compounds
*METHYLATION
*ENAMINES
- Language
- ISSN
- 0022-3263
The use of L-proline (30 mol %) and MW irradiation (13 W) with cooling promotes in a few hours the almost quantitative anomenzation of α-C-glycosylmethyl aldehydes into /3-isomers. An open-chain enamine-based mechanism is postulated for this transformation. The anomerization of a-ketones was instead achieved by the pyrrolidine/TFA couple and MW irradiation at 120 °C (enamine mechanism) and by DBU as Br∅nsted base (enolate mechanism). [ABSTRACT FROM AUTHOR]