四丁基氟化铵介导下由TMS保护的炔烃和醛直接合成α-联烯醇

Direct Synthesis of α-Allenols from TMS-Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride.

作者信息

Huang Xiaojun, Bugarin Alejandro

机构信息

Department of Chemistry and Biochemistry, University of Texas at Arlington, Planetarium Place Room 130, Arlington, TX, 76019, USA.

出版信息

Chemistry. 2016 Aug 26;22(36):12696-700. doi: 10.1002/chem.201603250. Epub 2016 Jul 28.

DOI:10.1002/chem.201603250

PMID:27401054

Abstract

A unique chemoselective synthesis of α-allenic alcohols is presented. Tetrabutylammonium fluoride (TBAF) mediated this transformation under mild reaction conditions. A range of functional groups is well-tolerated in this reaction, while affording adducts in moderate to excellent yields (48-96 %, average 76 %). Mechanistic studies, including the use of tetrabutylammonium hydroxide (TBAH), revealed that the hydroxide ion can be the responsible for the observed rearrangement.

摘要

本文介绍了一种独特的α-联烯醇化学选择性合成方法。四丁基氟化铵（TBAF）在温和的反应条件下介导了这种转化。该反应对一系列官能团具有良好的耐受性，同时以中等至优异的产率（48-96%，平均76%）提供加合物。包括使用四丁基氢氧化铵（TBAH）在内的机理研究表明，氢氧根离子可能是观察到的重排反应的原因。