Premium
Stereodynamics and absolute configuration of stereolabile atropisomers in 2,2‐dimethyl‐1‐aryl‐1‐indanols
Author(s) -
Casarini Daniele,
Mancinelli Michele,
Mazzanti Andrea,
Boschi Francesca
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20988
Subject(s) - atropisomer , chemistry , absolute configuration , aryl , chirality (physics) , circular dichroism , moiety , enantioselective synthesis , stereochemistry , axial chirality , cotton effect , computational chemistry , organic chemistry , catalysis , chiral symmetry , alkyl , physics , quantum mechanics , nambu–jona lasinio model , quark
We describe herein the investigation of the stereodynamic processes occurring in a series of 1‐aryl‐2,2‐dimethylindanols, by dynamic NMR. When the aryl moiety is a mesityl or a 2‐methyl‐1‐naphthyl, the rotational barrier exceeds the 25 kcal/mol, so that stable atropisomers are observed. In two cases, all the chiral‐atropisomeric species have been separated by enantioselective HPLC, and the comparison between theoretical and experimental electronic circular dichroism spectra allowed the absolute configuration assignment of all the isolated species to be obtained. Chirality, 2011. © 2011 Wiley‐Liss, Inc.