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Rhodium‐Catalyzed Cyclization of Diynes with Nitrones: A Formal [2+2+5] Approach to Bridged Eight‐Membered Heterocycles
Author(s) -
Wang Chunxiang,
Wang Dongping,
Yan Hao,
Wang Haolong,
Pan Bin,
Xin Xiaoyi,
Li Xincheng,
Wu Fan,
Wan Boshun
Publication year - 2014
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.201407394
Subject(s) - nitrone , rhodium , moiety , aryl , catalysis , ring (chemistry) , chemistry , substrate (aquarium) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , cycloaddition , alkyl , oceanography , geology
N‐aryl‐substituted nitrones were employed as five‐atom coupling partners in the rhodium‐catalyzed cyclization with diynes. In this reaction, the nitrone moiety served as a directing group for the catalytic CH activation of the N‐aryl ring. This formal [2+2+5] approach allows rapid access to bridged eight‐membered heterocycles with broad substrate scope. The results of this study may provide new insight into the chemistry of nitrones and find applications in the synthesis of other heterocycles.