Synthesis 2015; 47(16): 2414-2430
DOI: 10.1055/s-0034-1378736
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Shibo Xu
a  Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Shikuan Su
a  Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Huiting Zhang
a  Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Lumin Tian
a  Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Pengcheng Liang
a  Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Jiawen Chen
a  Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Yuan Zhang
a  Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Chunju Li
a  Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
,
Xueshun Jia*
a  Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
b  State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P. R. of China
,
Jian Li*
a  Department of Chemistry, Shanghai University, Shanghai, 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn   Email: lijian@shu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 17 April 2015

Accepted after revision: 05 June 2015

Publication Date:
24 July 2015 (eFirst)

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.

Supporting Information

 
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