Novel polyhydroxylated cyclic nitrones and N-hydroxypyrrolidines through BCl3-mediated deprotection

被引：28

作者：

Desvergnes, Stephanie ^{[1
]}

Vallee, Yannick ^{[1
]}

Py, Sandrine ^{[1
]}

机构：

[1] Univ Grenoble 1, CNRS, Dept Chim Mol SERCO UMR 5250, ICMG FR 2607, F-38041 Grenoble 09, France

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 14期

关键词：

D O I：

10.1021/ol8007759

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method to prepare a new class of carbohydrate-derived, enantiomerically pure polyhydroxypyrroline N-oxides from their alkoxy (protected) derivatives is presented. Boron trichloride is shown to cleave efficiently benzyl ethers and ketals without affecting the imine N-oxide functionality of nitrones. The same reagent (BCl3) also allowed the efficient synthesis of a polyhydroxylated N-hydroxypyrrolidine, giving access to a novel class of N-hydroxyiminosugars.

引用

页码：2967 / 2970

页数：4

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