Direct Access to 9/6‐Fused Cycles via Sequential Hydride Shift Mediated Double C(sp3)−H Bond Functionalization

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% iPr2NEt, the desired sequential [1,8]‐[1,5]‐hydride shift process proceeded smoothly to afford synthetically challe...

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Veröffentlicht in:	Advanced synthesis & catalysis 2023-02, Vol.365 (4), p.502-507
Hauptverfasser:	Nakamura, Issei, Anada, Masahiro, Sueki, Shunsuke, Makino, Kosho, Mori, Keiji
Format:	Artikel
Sprache:	eng
Schlagworte:	fused cycles hydride shift Hydrides internal redox reaction nine-membered ring Piperidine remote functionalization
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container_title	Advanced synthesis & catalysis
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creator	Nakamura, Issei Anada, Masahiro Sueki, Shunsuke Makino, Kosho Mori, Keiji
description	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% iPr2NEt, 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.
doi_str_mv	10.1002/adsc.202201354
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subjects	fused cycles hydride shift Hydrides internal redox reaction nine-membered ring Piperidine remote functionalization
title	Direct Access to 9/6‐Fused Cycles via Sequential Hydride Shift Mediated Double C(sp3)−H Bond Functionalization
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