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Dissecting the Gold(I)-Catalyzed Carboaminations of N-Allyl Tetrahydro-β-carbolines to Allenes
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-01-09 00:00:00 , DOI: 10.1021/acs.joc.7b02900
Valérian Gobé 1 , Maxime Dousset 1 , Pascal Retailleau 1 , Vincent Gandon 1, 2 , Xavier Guinchard 1
Affiliation  

N-Allyl tetrahydro-β-carbolines undergo gold-catalyzed cyclizations that lead to tetracyclic compounds, resulting from both ring closure and the transfer of the allylic group from the nitrogen to the carbon backbone. The final skeleton obtained depends on the nature of both the R2 group of the allene and the R3 group of the allylic residue. Mechanistic studies and DFT calculations allowed the determination of all the mechanistic pathways involved in these processes, stemming from a common intermediate that evolves differently according to the substituents nature.

中文翻译:

将金(I)催化的N-烯丙基四氢-β-咔啉的碳氨基化反应分解为异戊二烯

N-烯丙基四氢-β-咔啉经过金催化的环化反应,生成四环化合物,这是由于闭环和烯丙基从氮到碳主链的转移所致。所获得的最终骨架既取决于R的性质2组丙二烯的和将R 3基团的烯丙基残基。机理研究和DFT计算可确定这些过程中涉及的所有机理途径,这些途径均来自于根据取代基性质不同而变化的共同中间体。
更新日期:2018-01-09
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