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
Cited by
6 articles.
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