引用本文:
吴鸣虎, 陈祖兴, 李焰, 杨桂春. 非对映选择性合成科涅克内酯[J]. 应用化学,
2000, 17(1): 113-114.
Citation: WU Ming-Hu, CHEN Zu-Xing, LI Yan, YANG Gui-Chun. Diastereoselective Synthesis of (±)-trans-Cognac Lactone[J]. Chinese Journal of Applied Chemistry, 2000, 17(1): 113-114.
Citation: WU Ming-Hu, CHEN Zu-Xing, LI Yan, YANG Gui-Chun. Diastereoselective Synthesis of (±)-trans-Cognac Lactone[J]. Chinese Journal of Applied Chemistry, 2000, 17(1): 113-114.
非对映选择性合成科涅克内酯
English
Diastereoselective Synthesis of (±)-trans-Cognac Lactone
Abstract:
A new route to diastereoselective synthesis of (±)-trans-cognac lactone in five steps is described. The key intermediate methyl 3-formylbutanoate (4) was prepared from methy lcro tonate (1) in high yield.Addition of n-amylmagnesium bromide/cuprous iodide to the fo rmyl of (4), through fo rmation of seven-membered ring chelate which involved both carbonyl function groups of (4) and MgX or Cu as a central metal, afforded (±)-trans-cognac lactone (5) in 52% yield with high diastereoselectivity: ratio of trans to cisisomers was 97:3 by GC. The procedure had advantages of simplicity, high stereoselectivity of products and mild reaction conditions.
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Key words:
- trans-cognac lactone
- / butyrolactone
- / diastereoselective synthesis
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