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Organocatalytic Atroposelective Aldol Condensation: Synthesis of Axially Chiral Biaryls by Arene Formation
Author(s) -
Link Achim,
Sparr Christof
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201402441
Subject(s) - atropisomer , chemistry , axial chirality , chirality (physics) , condensation , aldol reaction , aldol condensation , ring (chemistry) , combinatorial chemistry , cascade , amine gas treating , organic chemistry , enantioselective synthesis , stereochemistry , catalysis , chromatography , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model , thermodynamics
Axially chiral compounds are of significant importance in modern synthetic chemistry and particularly valuable in drug discovery and development. Nonetheless, current approaches for the preparation of pure atropisomers often prove tedious. We demonstrate here a synthetic method that efficiently transfers the stereochemical information of a secondary amine organocatalyst into the axial chirality of tri‐ ortho ‐substituted biaryls. An aromatic ring is formed during the dehydration step of the described aldol condensation cascade, leading to highly enantioenriched binaphthyl derivatives. The fundamental course of the reaction is related to the biosynthesis of aromatic polyketides.