Use the olefin metathesis reaction for highly efficient β-cyclodextrin modification

被引：12

作者：

Ghera, BB ^{[1
]}

Fache, F ^{[1
]}

Parrot-Lopez, H ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, UMR 5181, Lab Chim Organ 2, F-69622 Villeurbanne, France

来源：

TETRAHEDRON | 2006年 / 62卷 / 20期

关键词：

beta-cyclodextrin; metathesis reaction; mono-functionalisation;

D O I：

10.1016/j.tet.2006.03.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of novel primary face mono-substituted P-cyclodextrin derivatives have been synthesised using the olefin metathesis reaction. Mono-6-allylamino-6-deoxy-beta-cyclodextrin easily synthesised by nucleophilic substitution of mono-6-tosyl-beta-cyclodextrin is the key synthon in the preparation of cyclodextrin derivatives mono-functionalised at the primary face by alkyl, aryl or perfluoroalkyl groups using Grubbs catalyst. In the cases of vinylbenzene and 1H, 1H, 2H-perfluoro-1-octene, the metathesis reactions yield with 95% stereoselectivity of the E-isomer. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4807 / 4813

页数：7

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