The Meyer-Schuster rearrangement for the synthesis of α,β-unsaturated carbonyl compounds
The Meyer-Schuster rearrangement for the synthesis of α,β-unsaturated carbonyl compounds
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DOI：
10.1039/b912099h
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发表时间：
2009-01-01
影响因子：
3.2
通讯作者：
Dudley, Gregory B.
中科院分区：
文献类型：
--
作者：
Engel, Douglas A.;Dudley, Gregory B.
Meyer-Schuster重排是炔丙醇通过形式1，3-羟基位移和互变异构转化为α，β-不饱和羰基化合物。与Meyer-Schuster反应相关的主要挑战是在炔丙醇可用的无数其他反应途径上选择性地促进所需的重排。本文介绍了迈耶-舒斯特反应的最新进展，包括几种改进范围的技术。每一种技术的优点和缺点进行了讨论，并突出了值得进一步研究的突出问题。研究和开发Meyer-Schuster重排的主要动机是作为制备α，β-不饱和羰基化合物的手段，作为两阶段烯化策略的一部分。
The Meyer-Schuster rearrangement is the conversion of propargyl alcohols into alpha,beta-unsaturated carbonyl compounds via a formal 1,3-hydroxyl shift and tautomerization. The major challenge associated with the Meyer-Schuster reaction is that of selectively promoting the desired rearrangement over the myriad other reaction pathways available to propargyl alcohols. This Perspective Article features recent advances in the Meyer-Schuster reaction, including several demonstrated techniques for improving the scope. Strengths and weaknesses of each technique are discussed, and outstanding problems that warrant further study are highlighted. The primary motivation for research and development of the Meyer-Schuster rearrangement is as a means of preparing alpha,beta-unsaturated carbonyl compounds as part of a two-stage olefination strategy.