Microwave-assisted organocatalytic anomerization of α-C-glycosylmethyl aldehydes and ketones

被引：37

作者：

Massi, Alessandro ^{[1
]}

Nuzzi, Andrea ^{[1
]}

Dondoni, Alessandro ^{[1
]}

机构：

[1] Univ Ferrara, Dipartimento Chim, Chim Organ Lab, I-44100 Ferrara, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 26期

关键词：

D O I：

10.1021/jo701959b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[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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页码：10279 / 10282

页数：4

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