Allyl, epoxy and glycosyl perfluoroimidates. One-pot preparation and reaction

被引：20

作者：

Nakajima, N ^{[1
]}

Saito, M ^{[1
]}

Kudo, M ^{[1
]}

Ubukata, M ^{[1
]}

机构：

[1] Toyama Prefectural Univ, Biotechnol Res Ctr, Imizu, Toyama 9390398, Japan

来源：

TETRAHEDRON | 2002年 / 58卷 / 18期

关键词：

activated dimethyl sulfoxide; dehydration; perfluoronitrile; perfluoroamide; perfluoroimidate; 3,3-sigmatropic rearrangement; acid-catalyzed cyclization; glycosylation;

D O I：

10.1016/S0040-4020(02)00305-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one-pot preparation of allyl, epoxy and glycosyl perfluoroimidates and their reaction are described. Volatile perfluoronitriles were generated from perfluoroamides with an 'activated dimethyl sulfoxide (DMSO) species at -78degreesC. Allyl, epoxy and glycosyl perfluoroimidates were prepared in 44-92% yield following in situ nucleophilic addition of alcohol and sugar derivatives to nitriles. The obtained trifluoroacetimidates were more stable than the trichloro analogue and were easily purified by SiO2 column chromatography and/or distillation. The 3,3-sigmatropic rearrangement of allylic analogues, acid-catalyzed cyclization of the epoxy analogues and glycosylation of sugar analogues were studied comparing with their corresponding trichloroacetimidates. The trifluoroacetimidates were considerably less reactive than trichloroacetimidates due to their electron-withdrawing substituents on the imidate carbon. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3579 / 3588

页数：10

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