Application of polymer-supported electrophilic reagents for the 1,2-functionalization of glycals

被引：46

作者：

Kirschning, A ^{[1
]}

Jesberger, M ^{[1
]}

Monenschein, H ^{[1
]}

机构：

[1] Tech Univ Clausthal, Inst Organ Chem, D-38678 Clausthal Zellerfeld, Germany

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(99)01925-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polymer-supported electrophilic reagents are prepared which efficiently add to carbohydrate-derived glycals under very mild conditions. Depending on the hypervalent reagent initially employed for oxidizing polymer-bound halides 1a or 1b both acetoxyhalogenations or azidoiodination can be carried out. With sugar-derived glycals, 2-deoxy-2-halo-pyranosyl acetates or azides are generated in excellent yield. Free hydroxy groups are tolerated. Even, fully unprotected glucal 23 can be employed for the short synthesis of 2-deoxy-2-iodo glycosyl acetates 24a,b. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8999 / 9002

页数：4

共 29 条

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