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Redox Tuning of a Direct Asymmetric Aldol Reaction
Author(s) -
Zhang Qiying,
Cui Xiuling,
Zhang Long,
Luo Sanzhong,
Wang Hui,
Wu Yangjie
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500070
Subject(s) - redox , moiety , aldol reaction , chemistry , ferrocene , catalysis , yield (engineering) , combinatorial chemistry , stereoselectivity , photochemistry , organic chemistry , materials science , electrochemistry , electrode , metallurgy
Presented herein is a redox tuning strategy for asymmetric aminocatalysis with a designed chiral ferrocenophane. Under redox control, the ferrocenophane catalyst efficiently catalyzes the asymmetric aldol reaction at room temperature with excellent yield and good stereoselectivity. Moreover, the redox‐active ferrocene moiety also served as phase‐tag to facilitate catalyst recovery and reuse. The catalyst can be reused for five cycles without much loss of activity. Ferrocenium of the oxidized ferrocenophane was proposed to serve as Lewis acidic site, thus accounting for the stereo control.