Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 46, Pages 20439-20444Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202008338
Keywords
asymmetric catalysis; copper; cyanation; radical reactions; etherification
Categories
Funding
- National Nature Science Foundation of China [21532009, 91956202, 21790330, 21821002]
- Science and Technology Commission of Shanghai Municipality [17XD1404500, 17QA1405200, 17JC1401200]
- strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- Key Research Program of Frontier Science of the Chinese Academy of Sciences [QYZDJSSWSLH055]
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The first copper-catalyzed asymmetric cyanation and etherification reactions of enamides have been established, where a carbon-centered radical adjacent to a nitrogen atom (CRAN) is enantioselectively trapped by a chiral copper(II) species. Moreover, the asymmetric cyanation of vinyl esters was disclosed as well. These reactions feature very mild reaction conditions and high functional group tolerance, and give a series of chiral alpha-cyano amides, alpha-cyano esters and alpha-hemiaminals in good yields with excellent enantioselectivity. The chiral alpha-cyano amides can be easily converted into enantioenriched 1,2-diamines and amino acids.
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