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Al(III)-Promoted Formation of All-Carbon Quaternary Centers from Aliphatic Tertiary Chlorides and Alkynyl Silanes
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2024-05-07 , DOI: 10.1021/acs.joc.4c00509
Paul Charki 1 , Daniel S. Müller 1
Affiliation  

Despite the accessibility of numerous alkynes through coupling or substitution reactions, the synthesis of trialkyl-substituted alkynes is still a major challenge. Within this context, we reexplored the electrophilic alkynyl substitution between tertiary aliphatic chlorides and silylated alkynes. We were able to demonstrate that this approach is significantly more general than originally demonstrated by Capozzi and even tolerates several functional groups. Furthermore, we report diastereoselective reactions which in some instances gave excellent diastereoselectivity (dr >95:5).

中文翻译:

Al(III) 促进脂肪族叔氯化物和炔基硅烷形成全碳四元中心

尽管可以通过偶联或取代反应获得许多炔烃,但三烷基取代的炔烃的合成仍然是一个重大挑战。在此背景下,我们重新探索了脂肪族叔氯和硅烷化炔之间的亲电炔基取代。我们能够证明这种方法比 Capozzi 最初证明的方法更加通用,甚至可以容忍多个功能组。此外,我们报告了非对映选择性反应,在某些情况下具有出色的非对映选择性(dr > 95:5)。
更新日期:2024-05-07
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