Atropoisomerism in Mono- and Diaryl-Substituted 4-Amino-2,6-lutidines

Marcin Górecki, Piotr Roszkowski, Dariusz Błachut, Jan K. Maurin, Armand Budzianowski, Jadwiga Frelek and Zbigniew Czarnocki

European Journal of Organic Chemistry
Volume 2016, Issue 17, Pages 2966–2971.
First published:
EurJOC (2016). 2016, 2966-2971 [doi:10.1002/ejoc.201600456]


The Suzuki–Miyaura reaction of 4-amino-3,5-dibromo-2,6-lutidine with various ortho-substituted phenylboronic acids resulted in the formation of a series of mono- and diarylated lutidines in the form of atropisomers. The absolute stereochemistry of the chiral compounds was established, in some cases, by X-ray crystal structure analysis and HPLC-ECD (ECD = electronic circular dichroism) in combination with time-dependent density functional theory (TDDFT) calculations.