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

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 hydrati...

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Published in:Synthesis (Stuttgart) 2015-08, Vol.47 (16), p.2414-2430
Main Authors: Xu, Shibo, Su, Shikuan, Zhang, Huiting, Tian, Lumin, Liang, Pengcheng, Chen, Jiawen, Zhang, Yuan, Li, Chunju, Jia, Xueshun, Li, Jian
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container_end_page 2430
container_issue 16
container_start_page 2414
container_title Synthesis (Stuttgart)
container_volume 47
creator Xu, Shibo
Su, Shikuan
Zhang, Huiting
Tian, Lumin
Liang, Pengcheng
Chen, Jiawen
Zhang, Yuan
Li, Chunju
Jia, Xueshun
Li, Jian
description 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.
doi_str_mv 10.1055/s-0034-1378736
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title Isocyanide-Based Multicomponent Reactions: Rapid Synthesis of a 5,5-Fused Bicyclic Skeleton from α,β-Unsaturated Ketones and Allenoates
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