Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL, USA.
Org Biomol Chem. 2009 Oct 21;7(20):4149-58. doi: 10.1039/b912099h. Epub 2009 Sep 14.
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.
迈尔-舒斯特重排反应是通过一个正式的 1,3-羟基移位和互变异构将丙炔醇转化为α,β-不饱和羰基化合物。与迈尔-舒斯特反应相关的主要挑战是选择性地促进所需的重排，而不是丙炔醇中存在的无数其他反应途径。这篇观点文章介绍了迈尔-舒斯特反应的最新进展，包括几种已证明的扩展反应范围的技术。讨论了每种技术的优缺点，并强调了需要进一步研究的突出问题。研究和开发迈尔-舒斯特重排反应的主要动机是作为制备α,β-不饱和羰基化合物的一种手段，作为两步烯烃化策略的一部分。
