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偕二酮-重氮酯两性离子盐的周环反应。一种合成高官能化间苯二酚的新策略。

Pericyclic reaction of a zwitterionic salt of an enedione-diazoester. A novel strategy for the synthesis of highly functionalized resorcinols.

机构信息

Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.

出版信息

Org Lett. 2010 Oct 1;12(19):4304-7. doi: 10.1021/ol101744h.

DOI:10.1021/ol101744h
PMID:20809648
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2945417/
Abstract

Enedione-diazoesters formed from 3-TBSO-2-diazo-3-butenoates undergo base-catalyzed pericyclization that with dinitrogen extrusion and methyl migration provide a novel and efficient route to 2-carboalkoxyresorcinols. Intercepting the intermediate enolate anion with methyl vinyl ketone leads to the corresponding 4-substituted 2-carboalkoxyresorcinol and suggests generalization of this methodology.

摘要

3-TBSO-2-重氮-3-丁烯酸酯形成的烯二酮-重氮酯经碱催化进行周环反应，通过消除氮气和甲基迁移，提供了一种新颖、高效的合成 2-羧酸甲氧基间苯二酚的方法。用甲基乙烯基酮捕获中间体烯醇负离子，得到相应的 4-取代 2-羧酸甲氧基间苯二酚，这表明该方法具有普遍性。

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