Optimization of Grignard ring-opening of α-brominated dioxolanes for the preparation of β-hydroxy-protected vinyl ethers by a three-step one-pot procedure

被引：4

作者：

Andre, Mathieu ^{[1
]}

Letribot, Boris ^{[2
]}

Bayle, Martine ^{[1
]}

Mounetou, Emmanuelle ^{[1
]}

Chezal, Jean-Michel ^{[1
]}

机构：

[1] U990 INSERM, F-63000 Clermont Ferrand, France

[2] Univ La Rochelle, CNRS, UMR 7266, Littoral Environm & Soc LIENSs, F-17042 La Rochelle 01, France

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 45期

关键词：

Grignard reaction; Dioxolane ring-opening; Enol ethers; Vinyl ethers; alpha-Brominated dioxolanes; FACILE SYNTHESIS; ENOL ETHERS; PLASMALOGENS;

D O I：

10.1016/j.tetlet.2012.08.144

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

Aliphatic, cyclic, and aromatic benzoate-protected gamma-hydroxy enol ethers were prepared from alpha-brominated dioxolanes by a three-step reaction procedure and a one-pot protocol involving Grignard reagent formation, ring-opening, and final benzoate protection. Additionally, tert-butyldiphenylsilyl, acetate, and 4,4'-dimethoxytrityl were also successfully used as alternative protecting groups. (C) 2012 Elsevier Ltd. All rights reserved.

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页码：6107 / 6110

页数：4

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