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Atropoisomerism in Mono‐ and Diaryl‐Substituted 4‐Amino‐2,6‐lutidines
Author(s) -
Górecki Marcin,
Roszkowski Piotr,
Błachut Dariusz,
Maurin Jan K.,
Budzianowski Armand,
Frelek Jadwiga,
Czarnocki Zbigniew
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600456
Subject(s) - chemistry , atropisomer , time dependent density functional theory , circular dichroism , absolute configuration , density functional theory , stereochemistry , computational chemistry
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.