Synthesis of Functionalized Alkylidenecyclopropanes by Ireland鈥揅laisen Rearrangement of Cyclopropenylcarbinyl Esters
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- 作者：Guillaume Ernouf ; Jean-Louis Brayer ; Beno卯t Foll茅as ; Jean-Pierre Demoute ; Christophe Meyer ; Janine Cossy
- 刊名：Organic Letters
- 出版年：2015
- 出版时间：August 7, 2015
- 年：2015
- 卷：17
- 期：15
- 页码：3786-3789
- 全文大小：423K
- ISSN：1523-7052
文摘
Glycolates or glycinates derived from diversely substituted secondary cyclopropenylcarbinols have been involved for the first time in an Ireland鈥揅laisen rearrangement. This reaction allows an efficient and stereoselective access to highly functionalized alkylidenecyclopropanes possessing an 伪-hydroxy or 伪-amino acid subunit, which in turn are valuable precursors of substituted cyclopropanes by diastereoselective hydrogenation of the exocyclic alkene.