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

Author:

Nakamura Issei1,Anada Masahiro23,Sueki Shunsuke23,Makino Kosho23,Mori Keiji1ORCID

Affiliation:

1. Department of Applied Chemistry Graduate School of Engineering Tokyo University of Agriculture and Technology 2-24-16 Nakacho 184-8588 Koganei Tokyo Japan

2. Faculty of Pharmacy Musashino University 202-8585 Nishitokyo Tokyo Japan

3. Research Institute of Pharmaceutical Sciences Musashino University 202-8585 Nishitokyo Tokyo Japan

Abstract

AbstractWe 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.magnified image

Funder

Japan Society for the Promotion of Science

Naito Foundation

Publisher

Wiley

Subject

General Chemistry

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