通过一种新型的内酯化-消除重排反应区域选择性合成α-甲基2-亚甲基戊二酸酯。
Regioselective synthesis of alpha-methyl 2-methyleneglutarate via a novel lactonization-elimination rearrangement.
作者信息
Bartley David M, Coward James K
机构信息
Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
出版信息
J Org Chem. 2006 Jan 6;71(1):372-4. doi: 10.1021/jo051854a.
Abstract
[reaction: see text] A facile route to the alpha-methyl ester of 2-methyleneglutarate via a three-step sequence from 3-hydroxymethylcyclopentene is described. Regioselective formation of the monoacid from a diester precursor proceeds via a novel fluoride-mediated, tandem deprotection/rearrangement of O-silyl 2-(hydroxymethyl)dimethylglutarate.
摘要
[反应：见正文] 描述了一种从3-羟甲基环戊烯经三步反应制备2-亚甲基戊二酸α-甲酯的简便方法。由二酯前体区域选择性地形成单酸是通过一种新型氟化物介导的O-硅基-2-(羟甲基)二甲基戊二酸酯的串联脱保护/重排反应进行的。
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