A new synthesis of β,γ-unsaturated esters and allenic esters with construction of a carbon–carbon bond between α- and β-positions by the reaction of magnesium alkylidene carbenoids with lithium ester enolates
作者:Tsuyoshi Satoh、Hiroaki Kaneta、Ayako Matsushima、Masanobu Yajima
DOI:10.1016/j.tetlet.2009.08.102
日期:2009.11
Treatment of lithium ester enolates with magnesium alkylidene carbenoids, generated from 1-chlorovinyl p-tolyl sulfoxides with isopropylmagnesium chloride via the sulfoxide–magnesium exchange reaction, gave β,γ-unsaturated esters in moderate to good yields. When this reaction was conducted with the lithium ester enolates of α-chlorocarboxylic acid esters, allenic esters were obtained. This procedure
用亚异丙基氯化镁经亚砜-镁交换反应,用1-亚氯乙烯基对甲苯基亚砜生成的亚烷基镁类苯甲酸酯处理酯化锂烯醇化物,得到中等产率至良好产率的β,γ-不饱和酯。当用α-氯代羧酸酯的锂酯烯酸酯进行该反应时,得到烯丙酸酯。该方法为从酮合成β,γ-不饱和酯和烯丙酸酯提供了空前的方法,并在α-和β-位之间建立了碳-碳键。