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Phosphine‐Catalyzed Activation of Vinylcyclopropanes: Rearrangement of Vinylcyclopropylketones to Cycloheptenones
Author(s) -
Wu Jun,
Tang Yuhai,
Wei Wen,
Wu Yong,
Li Yang,
Zhang Junjie,
Zheng Yuansuo,
Xu Silong
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201800555
Subject(s) - phosphine , synthon , chemistry , catalysis , substrate (aquarium) , ring (chemistry) , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , oceanography , geology
We report a phosphine‐catalyzed activation of electron‐deficient vinylcyclopropanes (VCPs) to generate an ambident C 5 synthon that is poised to undergo consecutive reactions. The utility of the activation is demonstrated in a phosphine‐catalyzed rearrangement of vinylcyclopropylketones to cycloheptenones in good yields with a broad substrate scope. Mechanistic investigations support a stepwise process comprising homoconjugate addition, water‐assisted proton transfer, and 7‐ endo ‐trig S N 2′ ring closure.
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