Stereoselection in the prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral
Stereoselection in the prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral
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DOI：
10.1021/ol991315q
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发表时间：
2000-01-27
期刊：
影响因子：
5.2
通讯作者：
Wurster, JA
中科院分区：
文献类型：
--
作者：
Hanaki, N;Link, JT;Wurster, JA
烯丙基二醇与不对称酮的缩合反应具有很高的立体选择性，当酮的α取代基大小相差很大时，生成2，2-二取代的4-酰基四氢呋喃。这种Prins-Pinacol缩合反应是对映体选择性合成(-)-柠檬酸病毒的中心战略步骤。
The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the alpha-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.