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Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2023-10-23 , DOI: 10.3762/bjoc.19.118
Aaron H Shoemaker 1 , Elizabeth A Foker 1 , Elena P Uttaro 1 , Sarah K Beitel 1 , Daniel R Griffith 1
Affiliation  

Abstract

The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η4-diene complex with Fe(CO)3) in a short sequence of steps: 1) nucleophilic amine addition and subsequent Boc-protection, 2) photochemical demetallation of the iron complex, and 3) an intramolecular Heck reaction. Minor modifications to the protocol enabled access to the related 2-azabicyclo[4.4.1]undecane system, albeit in lower yield.

Beilstein J. Org. Chem. 2023, 19, 1615–1619. doi:10.3762/bjoc.19.118



中文翻译:

通过分子内 Heck 反应从三羰基(托酮)铁合成 7-氮杂双环[4.3.1]癸烷环系统

摘要

7-氮杂双环[4.3.1]癸烷环系统是许多生物活性生物碱所共有的,是通过简短的步骤从托酮(通过其 η 4 -二烯与 Fe(CO) 3的复合物)获得的:1)亲核胺加成和随后的 Boc 保护,2) 铁配合物的光化学脱金属,以及 3) 分子内 Heck 反应。对方案进行少量修改即可访问相关的 2-氮杂双环[4.4.1]十一烷系统,尽管产率较低。

贝尔斯坦 J. 组织。化学。 2023, 19, 1615–1619。doi:10.3762/bjoc.19.118

更新日期:2023-10-23
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