Enantioselective Cycloadditions of Vinyl Cyclopropanes and Nitroolefins for Functionally and Optically Enriched Nitrocyclopentanes

Palladium‐catalyzed enantioselective cycloaddition of vinyl cyclopropane dicarbonitriles and nitroolefins was achieved to generate structurally and optically enriched nitrocyclopentanes with three consecutive chiral carbon centers in up to 96 % yield and with up to 92 % ee. The two diastereoisomers...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2015-01, Vol.4 (1), p.28-32
Main Authors: Li, Wen-Ke, Liu, Ze-Shui, He, Long, Kang, Tai-Ran, Liu, Quan-Zhong
Format: Article
Language:English
Subjects:
cycloaddition
nitroalkenes
nitrocyclopentanes
Organic chemistry
palladium
vinyl cyclopropane dicarbonitriles
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Summary:Palladium‐catalyzed enantioselective cycloaddition of vinyl cyclopropane dicarbonitriles and nitroolefins was achieved to generate structurally and optically enriched nitrocyclopentanes with three consecutive chiral carbon centers in up to 96 % yield and with up to 92 % ee. The two diastereoisomers produced in each reaction are readily separable by simple chromatography. The present method allows the preparation of both diastereoisomers in optically enriched form. Spinning the vinyl: Palladium catalyzed enantioselective (3+2) cycloadditions of vinyl cyclopropane dicarbonitriles and nitroolefins were realized for constructing structurally and optically enriched nitrocyclopentanes.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201402219