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

Dinghai Wang; Fei Wang; Pinghong Chen; Zhenyang Lin; Guosheng Liu

doi:10.1002/anie.201611850

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

Angew Chem Int Ed Engl. 2017 Feb 13;56(8):2054-2058. doi: 10.1002/anie.201611850. Epub 2017 Jan 23.

Authors

Dinghai Wang¹, Fei Wang¹, Pinghong Chen¹, Zhenyang Lin², Guosheng Liu¹

Affiliations

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
² Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China.

PMID: 28111866
DOI: 10.1002/anie.201611850

Abstract

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/Cu^II 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.

Keywords: alkenes; asymmetric catalysis; copper; intermolecular reactions; radical reactions.

Publication types

Research Support, Non-U.S. Gov't