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通过对、和苄氧基-丁基苯甲酰胺进行维蒂希重排制备二芳基甲醇。

Access to Diarylmethanols by Wittig Rearrangement of , , and Benzyloxy--Butylbenzamides.

作者信息

Aitken R Alan, Harper Andrew D, Inwood Ryan A, Slawin Alexandra M Z

机构信息

EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, U.K.

出版信息

J Org Chem. 2022 Apr 1;87(7):4692-4701. doi: 10.1021/acs.joc.1c03160. Epub 2022 Mar 14.

DOI:10.1021/acs.joc.1c03160
PMID:35286089
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9007461/
Abstract

The -butyl amide group, CONHBu, has been found to be an effective promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy, and fluoro, although not with nitro and, unexpectedly, is applicable to as well as and isomeric series.

摘要

已发现丁基酰胺基团CONHBu是芳基苄基醚[1,2]-维蒂希重排的有效促进剂，因此可从简单的羟基苯甲酸衍生物出发，通过两步合成得到异构体纯的取代二芳基甲醇。该方法与包括甲基、甲氧基和氟在内的多种官能团兼容，尽管与硝基不兼容，而且出乎意料的是，它适用于以及和异构体系列。

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