期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 365, 期 4, 页码 502-507出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202201354
关键词
internal redox reaction; hydride shift; remote functionalization; nine-membered ring; fused cycles
We have developed a sequential hydride shift process involving a [1,8]-hydride shift, leading to the synthesis of nine-membered carbocycle-fused piperidine derivatives in good yields. The use of 30 mol% Yb(OTf)(3) and 10 mol% iPr(2)NEt as catalysts is crucial for the success of this reaction.
We have developed a sequential hydride shift process involving a [1,8]-hydride shift. When cinnamylidene malonates having a biphenyl core were treated with 30 mol% Yb(OTf)(3) and 10 mol% iPr(2)NEt, the desired sequential [1,8]-[1,5]-hydride shift process proceeded smoothly to afford synthetically challenging nine-membered carbocycle-fused piperidine derivatives in good chemical yields (up to 77%). Notably, the desired nine-membered carbocycles could not be obtained by a single [1,8]-hydride shift/cyclization process, suggesting that the employment of the sequential system is crucial to achieving the reaction.
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