Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Org Lett. 2010 Oct 1;12(19):4304-7. doi: 10.1021/ol101744h.
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.
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。