Isocyanide-Based Multicomponent Reactions: Rapid Synthesis of a 5,5-Fused Bicyclic Skeleton from α,β-Unsaturated Ketones and Allenoates

Shibo Xu; Shikuan Su; Huiting Zhang; Lumin Tian; Pengcheng Liang; Jiawen Chen; Yuan Zhang; Chunju Li; Xueshun Jia; Jian Li

doi:10.1055/s-0034-1378736

Synthesis, Table of Contents

Synthesis 2015; 47(16): 2414-2430
DOI: 10.1055/s-0034-1378736

special topic

Isocyanide-Based Multicomponent Reactions: Rapid Synthesis of a 5,5-Fused Bicyclic Skeleton from α,β-Unsaturated Ketones and Allenoates

Shibo Xu

^aDepartment of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China Email: xsjia@mail.shu.edu.cn Email: lijian@shu.edu.cn

,

Shikuan Su

^aDepartment of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China Email: xsjia@mail.shu.edu.cn Email: lijian@shu.edu.cn

,

Huiting Zhang

^aDepartment of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China Email: xsjia@mail.shu.edu.cn Email: lijian@shu.edu.cn

,

Lumin Tian

^aDepartment of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China Email: xsjia@mail.shu.edu.cn Email: lijian@shu.edu.cn

,

Pengcheng Liang

^aDepartment of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China Email: xsjia@mail.shu.edu.cn Email: lijian@shu.edu.cn

,

Jiawen Chen

^aDepartment of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China Email: xsjia@mail.shu.edu.cn Email: lijian@shu.edu.cn

,

Yuan Zhang

^aDepartment of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China Email: xsjia@mail.shu.edu.cn Email: lijian@shu.edu.cn

,

Chunju Li

^aDepartment of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China Email: xsjia@mail.shu.edu.cn Email: lijian@shu.edu.cn

,

Xueshun Jia*

^aDepartment of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China Email: xsjia@mail.shu.edu.cn Email: lijian@shu.edu.cn

^bState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P. R. of China

,

Jian Li*

^aDepartment of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China Email: xsjia@mail.shu.edu.cn Email: lijian@shu.edu.cn

› Author Affiliations

Abstract

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Abstract

An efficient multicomponent reaction of isocyanides, allenoates, and α,β-unsaturated ketones is disclosed, thus providing rapid access for the synthesis of bicyclic skeletons. From a mechanistic standpoint, the present cycloaddition proceeds through cascade cycloaddition followed by hydration and intramolecular cyclization. Several controlled experiments are also conducted to gain further insight into the reaction mechanism; some valuable and interesting findings were observed during this process. To enrich the structural diversity, 3-(2-oxoethylene)indolinones (i.e. with an α,β-unsaturated ketone at position 3) were also found to be compatible in this reaction. In addition, this method is also characterized by its broad substrate scope, mild conditions, and high efficiency, which makes it valuable for further application.

Key words

isocyanide - multicomponent reaction - allenoate - bicyclic skeleton - α,β-unsaturated ketone

Full Text

References

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Supporting Information