环丙烯酮催化醇与甲磺酸酯离子的取代反应。
Cyclopropenone catalyzed substitution of alcohols with mesylate ion.
机构信息
Department of Chemistry, Columbia University, New York, New York 10027, USA.
出版信息
Org Lett. 2013 Jan 4;15(1):38-41. doi: 10.1021/ol302970c. Epub 2012 Dec 13.
PMID:23237617
Abstract
The cyclopropenone catalyzed nucleophilic substitution of alcohols by methanesulfonate ion with inversion of configuration is described. This work provides an alternative to the Mitsunobu reaction that avoids the use of azodicarboxylates and generation of hydrazine and phosphine oxide byproducts. This transformation is shown to be compatible with a range of functionality. A cyclopropenone scavenge strategy is demonstrated to aid purification.
摘要
描述了环丙烯酮催化的醇与甲磺酸离子的亲核取代反应，构型发生翻转。该工作提供了一种替代 Mitsunobu 反应的方法，避免了使用偶氮二甲酸酯以及生成肼和氧化膦副产物。该转化与一系列官能团兼容。还展示了一种环丙烯酮清除策略来辅助纯化。
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