Anionic Bisoxazoline Ligands Enable Copper-Catalyzed Asymmetric Radical Azidation of Acrylamides

Autor:	Zhenyang Lin, Fei Wang, Lianqian Wu, Pinhong Chen, Guosheng Liu, Dunqi Wu, Zhihan Zhang
Rok vydání:	2020
Předmět:	chemistry.chemical_classification 010405 organic chemistry Chemistry Ligand Alkene Radical Enantioselective synthesis General Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound Monomer Polymer chemistry Organic synthesis Azide
Zdroj:	Angewandte Chemie (International ed. in English). 60(13)
ISSN:	1521-3773
Popis:	Asymmetric radical azidation for the synthesis of chiral alkylazides remains a tremendous challenge in organic synthesis. We report here an unprecedented highly enantioselective radical azidation of acrylamides catalyzed by 1 mol% of copper catalyst, and arrays of acrylamides were converted to the corresponding alkylazides in high yield with good to excellent enantioselectivities. Notably, employing anionic cyano-bisoxazoline (CN-Box) ligand is crucial, which generates a monomeric Cu(II) azide species, rather than a dimeric Cu(II) azide intermediate, for this highly enantioselective radical azidation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1620b0be743d5e028b001cc9b85a15f6 https://pubmed.ncbi.nlm.nih.gov/33354830 Zobrazit plný text záznamu Plný text