化学
催化作用
赫克反应
组合化学
胺气处理
钯
立体化学
有机化学
作者
Vinod G. Landge,Ankita Mishra,Waruna Thotamune,Audrey Bonds,Indunil Alahakoon,Ajith Karunarathne,Michael C. Young
出处
期刊:Chem catalysis
[Elsevier]
日期:2023-11-01
卷期号:3 (11): 100809-100809
标识
DOI:10.1016/j.checat.2023.100809
摘要
An outstanding challenge in the Pd-catalyzed functionalization of allylamines is the control of stereochemistry. Terminal alkenes preferentially undergo Heck-type reactions, while internal alkenes may undergo a mixture of Heck and C–H activation reactions that give mixtures of stereochemical products. In the case of unprotected allylamines, the challenge in achieving C–H activation is that facile in situ formation of Pd nanoparticles leads to preferential formation of trans rather than cis substituted products. In this study, we have demonstrated the feasibility of using mono-protected amino acid ligands as metal-protecting groups to prevent aggregation and reduction, allowing the selective synthesis of free cis-arylated allylamines. This method complements Heck-selective methods, allowing complete stereochemical control over the synthesis of cinnamylamines, an important class of amine that can serve as therapeutics directly or as advanced intermediates. To highlight the utility of the methodology, we have demonstrated rapid access to mu (γ) opioid receptor ligands.
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