钯催化的糖基亚氨酸酯重排反应：α-和β-N-糖基三氯乙酰胺的形成

Palladium-catalyzed glycal imidate rearrangement: formation of alpha- and beta-N-glycosyl trichloroacetamides.

作者信息

Yang Jaemoon, Mercer Gregory J, Nguyen Hien M

机构信息

Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA.

出版信息

Org Lett. 2007 Oct 11;9(21):4231-4. doi: 10.1021/ol701778z. Epub 2007 Sep 19.

DOI:10.1021/ol701778z

PMID:17880097

Abstract

A novel palladium(II)-catalyzed stereoselective synthesis of alpha- and beta-N-glycosyl trichloroacetamides has been developed. The alpha- and beta-selectivity at the anomeric carbon depends on the nature of the palladium-ligand catalyst. While the cationic palladium(II) promotes the alpha-selectivity, the neutral palladium(II) favors the beta-selectivity.

摘要

已开发出一种新型钯（II）催化的α-和β-N-糖基三氯乙酰胺的立体选择性合成方法。异头碳上的α-和β-选择性取决于钯-配体催化剂的性质。阳离子钯（II）促进α-选择性，而中性钯（II）有利于β-选择性。