Asymmetric Vinylogous Michael Addition/Cyclization Cascade Reaction for the Construction of Diversely Structured Spiro- Oxindole Skeletons

We present the first organocatalytic asymmetric vinylogous Michael/cyclization reaction of α,α‐dicyanoalkenes with 3‐alkylideneoxindoles. A series of diversely structured spiro‐oxindole skeletons was smoothly delivered with excellent yields and stereoselectivity control (94–99% yields, >20:1 dr a...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2013-11, Vol.355 (16), p.3119-3123
Main Authors: Shi, Xiao-Mei, Dong, Wei-Ping, Zhu, Li-Ping, Jiang, Xian-Xing, Wang, Rui
Format: Article
Language:English
Subjects:
asymmetric catalysis
Asymmetry
cascade reactions
Cascades
Catalysis
Construction
dicyanoalkenes
Michael addition
Michael reaction
organocatalysis
Stereoselectivity
Synthesis
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Summary:We present the first organocatalytic asymmetric vinylogous Michael/cyclization reaction of α,α‐dicyanoalkenes with 3‐alkylideneoxindoles. A series of diversely structured spiro‐oxindole skeletons was smoothly delivered with excellent yields and stereoselectivity control (94–99% yields, >20:1 dr and 91 to >99% ee).
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201300329