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Chiral Guanidine/Copper Catalyzed Asymmetric Azide‐Alkyne Cycloaddition/[2+2] Cascade Reaction
Author(s) -
Guo Songsong,
Dong Pei,
Chen Yushuang,
Feng Xiaoming,
Liu Xiaohua
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.201810679
Subject(s) - guanidine , cycloaddition , alkyne , chemistry , azide , ketenimine , copper , combinatorial chemistry , catalysis , cascade reaction , isatin , salt (chemistry) , sulfonyl , medicinal chemistry , polymer chemistry , organic chemistry , alkyl
We report the development of a chiral guanidine‐based copper(I) catalyst for the asymmetric azide‐alkyne cycloaddition/[2+2] cascade reaction. Optically active spiroazetidinimine oxindoles were constructed by trapping the ketenimine species under mild reaction conditions. High level of enantioinduction and excellent isolated yields were achieved in the three‐component reaction of various isatin‐derived ketimines, sulfonyl azides, and terminal alkynes. Control experiments and X‐ray crystallography were used to probe into the interaction of chiral guanidinium salt with copper salt.