Michael Reaction Inspired Atroposelective Construction of Axially Chiral Biaryls

Autor:	Shengyi Yan, Qiuling Song, Shaoyu Li, Shao-Hua Xiang, Wang Xia, Bin Tan
Rok vydání:	2020
Předmět:	Phosphoramidite Atropisomer Chemistry Chiral ligand General Chemistry Optically active 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Catalysis 0104 chemical sciences Colloid and Surface Chemistry Michael reaction Axial symmetry
Zdroj:	Journal of the American Chemical Society. 142:7322-7327
ISSN:	1520-5126 0002-7863
Popis:	The first copper-catalyzed atroposelective Michael-type addition between azonaphthalenes and arylboronic acids for the construction of biaryl atropisomers was established using a novel BINOL-derived phosphoramidite as a chiral ligand. A broad range of atropisomeric biaryls were obtained with good efficiency, and the practicality of this approach was verified by versatile transformations toward axially chiral ligands, catalysts, and other functional atropisomers. This set of catalytic systems successfully inhibited the routine 1,2-addition and promoted the formation of an aryl-aryl chiral axis. Meanwhile, this strategy bypassed the use of an oxidant as well as the harsh conditions normally necessary for transition-metal-mediated arene C-H coupling with arylboronic acids as an arylation counterpart, offering a straightforward alternative to access optically active biaryls.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a7fe15bbfbd9effb962053d6610d152e https://doi.org/10.1021/jacs.0c01963 Zobrazit plný text záznamu