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Quinine‐Catalyzed Asymmetric Synthesis of 2,2′‐Binaphthol‐Type Biaryls under Mild Reaction Conditions
Author(s) -
Moliterno Mauro,
Cari Riccardo,
Puglisi Antonio,
Antenucci Achille,
Sperandio Céline,
Moretti Erica,
Di Sabato Antonio,
Salvio Riccardo,
Bella Marco
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201601660
Subject(s) - atropisomer , chemistry , enantiomer , reagent , yield (engineering) , catalysis , enantioselective synthesis , stereoselectivity , combinatorial chemistry , organocatalysis , organic chemistry , materials science , metallurgy
Simple quinine as an organocatalyst mediates the addition of various naphthols to halogenated quinones to afford non‐ C 2 ‐symmetrical, axially chiral biaryl products, which are promising compounds as chiral ligands and organocatalysts. The rotational barrier required to have two distinct atropisomers has been evaluated in the products generated from the addition of naphthols to various quinones by means of DFT calculations and HPLC. The use of halogenated quinones as reagents was necessary to have configurationally stable enantiomeric products which can be obtained in good yield and stereoselectivity. These compounds have also been prepared in gram quantities and recrystallized to near enantiopurity.