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非对映选择性合成威士忌内酯 被引量:4

Diastereoselective Synthesis of (±)-trans-Whisky Lactone
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摘要 报道威士忌内酯的非对映选择性合成。该合成路线包括 5步反应。从巴豆酸甲酯出发制得重要中间产物3 -甲酰基丁酸甲酯。利用 3 -甲酰基丁酸甲酯的两个羰基与金属离子的螯合作用来控制其与正丁基溴化镁的加成反应 ,立体选择性地得到威士忌内酯。经气相色谱测定表明 ,产物反、顺异构体之比为 92∶ A new diastereoselective route composed of five steps to (±) [WT5BX]trans whisky lactone([ST5HZ]5) was investigated. The key intermediate methyl 3 formylbutanoate([ST5HZ]4) was prepared from methyl crotonate([ST5HZ]1) in high yield. Addition of [WT5BX]n butylmagnesium bromide/cuprous iodide to the formyl of [ST5HZ]4, through formation of seven menbered ring chelate which invoved both carbonyl functions of [ST5HZ]4 and MgX or Cu as a central metal, afforded [ST5HZ]5 with high diastereoselectivity and yield of 52%. GC determination showed that the ratio of trans to cis isomer in the product was 92∶8. This procedure had advantages of short route, high stereoselective yield and mild conditions.
出处 《合成化学》 CAS CSCD 2001年第2期167-169,共3页 Chinese Journal of Synthetic Chemistry
基金 湖北省教育厅优秀青年人才项目 !( 2 0 0 0 B490 0 1)
关键词 食用香料 昆虫信息素 威士忌内酯 丁内酯 非对映选择性合成 巴豆酸甲酯 flavor sex pheromone (±) trans whisky lactone butyrolactone diastereoselective synthesis
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