The use of L-proline (30 mol%) and MW irradiation (13 W) with cooling promote in a few hours the almost quantitative anomerization of alpha-C-glycosylmethyl aldehydes into -isomers. An open chain enamine-based mechanism is postulated for this transformation. The anomerization of -ketones was instead achieved by the pyrrolidine/TFA couple and MW irradiation at 120 °C (enamine mechanism) and by DBU as Brønsted base (enolate mechanism).
Microwave-Assisted Organocatalytic Anomerization of alpha-C-Glycosylmethyl Aldehydes and Ketones
MASSI, Alessandro;DONDONI, Alessandro;NUZZI, Andrea
2007
Abstract
The use of L-proline (30 mol%) and MW irradiation (13 W) with cooling promote in a few hours the almost quantitative anomerization of alpha-C-glycosylmethyl aldehydes into -isomers. An open chain enamine-based mechanism is postulated for this transformation. The anomerization of -ketones was instead achieved by the pyrrolidine/TFA couple and MW irradiation at 120 °C (enamine mechanism) and by DBU as Brønsted base (enolate mechanism).File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
