Lewis‐Base‐Catalyzed Annulations of Nitroallylic Acetates as C 3 Synthons with Electron‐Deficient Alkenes

2‐Nitroallylic acetates have been demonstrated to be versatile C 3 synthons in Lewis‐base‐catalyzed annulation reactions. Catalyzed by PhPMe 2 (20 mol %), they readily undergo a cascade [3+2] annulation/allylic alkylation reaction with electron‐deficient alkenes to provide cyclopentenes and even spi...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2014-08, Vol.3 (8), p.877-885
Main Authors: Chen, Rongshun, Fan, Xia, Gong, Junyu, He, Zhengjie
Format: Article
Language:English
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Summary:2‐Nitroallylic acetates have been demonstrated to be versatile C 3 synthons in Lewis‐base‐catalyzed annulation reactions. Catalyzed by PhPMe 2 (20 mol %), they readily undergo a cascade [3+2] annulation/allylic alkylation reaction with electron‐deficient alkenes to provide cyclopentenes and even spirocyclopenteneoxindoles in moderate to good yields and high diastereoselectivity. Under the catalysis of 4‐dimethylaminopyridine (20 mol %), 2‐nitroallylic acetates also undergo a [3+3] annulation reaction with 1,1‐dicyanoalkenes to give cyclohexenes. This work further broadens the scope of the Lewis‐base‐catalyzed annulation protocol for modified allylic derivatives.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201402059