Enantioselective Copper‐Catalyzed Intermolecular Amino‐ and Azidocyanation of Alkenes in a Radical Process

Asymmetric copper‐catalyzed intermolecular amino‐ and azidocyanation reactions of alkenes have been developed that proceed via a radical process in which a key benzylic radical intermediate is enantioselectively trapped by a chiral Box/CuII cyanide complex. A variety of enantiomerically enriched β‐a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-02, Vol.56 (8), p.2054-2058
Main Authors: Wang, Dinghai, Wang, Fei, Chen, Pinghong, Lin, Zhenyang, Liu, Guosheng
Format: Article
Language:English
Subjects:
Alkenes
asymmetric catalysis
Bioactive compounds
Chemical reactions
Copper
Cyanides
Enantiomers
intermolecular reactions
Optical activity
radical reactions
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Summary:Asymmetric copper‐catalyzed intermolecular amino‐ and azidocyanation reactions of alkenes have been developed that proceed via a radical process in which a key benzylic radical intermediate is enantioselectively trapped by a chiral Box/CuII cyanide complex. A variety of enantiomerically enriched β‐amino/azido alkylnitriles were efficiently synthesized. The β‐azido alkylnitriles could be converted into a series of highly valuable optically active amine‐based building blocks and bioactive compounds. A radical process is involved in the asymmetric copper‐catalyzed intermolecular amino‐ and azidocyanation of alkenes developed herein. A variety of enantiomerically enriched β‐amino/azido alkylnitriles were efficiently synthesized. The azidocyanation products were further converted into a series of optically active building blocks and bioactive compounds.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201611850