New perspectives for Lewis acid-catalyzed [2+2] cycloadditions of allenoates

路易斯酸催化[2 2]联烯酸酯环加成的新视角

• 批准号: 361417940
• 负责人: Professor Dr. Johannes M. Wahl
• 金额: --
• 依托单位: Department Chemie
• 依托单位国家: 德国
• 项目类别: Research Fellowships
• 财政年份: 2017
• 资助国家: 德国
• 起止时间: 2016-12-31 至 2018-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/361417940?language=en
• 关键词: New; perspectives; Lewis; acid; catalyzed

The objective of this proposal is the synthesis of hebelophyllene E, a naturally occurring sesquiterpene, which was isolated from the ectomycorrhizal fungus Hebeloma longicaudum in the late 1990s. In the context of this project, we have developed an enantioselective Lewis-acid catalyzed [2+2] cycloaddition followed by a ligand controlled copper hydride reduction to access the cis-fused cyclobutane motif. Thus, the goal is to apply these findings in the synthesis of hebelophyllene E and demonstrate that our methodology can be used early in a synthetic sequence as well as late stage using highly functionalized alkenes.

该建议的目的是合成hebelophyllene E，一种天然存在的倍半萜，其在20世纪90年代末从外生菌根真菌Hebeloma longicaudum中分离。在这个项目的背景下，我们已经开发了一种对映选择性的路易斯酸催化的[2+2]环加成，然后由配体控制的氢化铜还原访问顺式稠合环丁烷基序。因此，我们的目标是将这些发现应用于hebelopyllene E的合成中，并证明我们的方法可以用于合成序列的早期以及使用高度官能化的烯烃的后期。

项目成果

Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

• DOI: 10.1021/jacs.8b10008
• 发表时间: 2018-11-21
• 期刊: Journal of the American Chemical Society
• 影响因子: 15
• 作者: Wahl JM;Conner ML;Brown MK
• 通讯作者: Brown MK