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Updated: Mar 22, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Quinine-Catalyzed Asymmetric Synthesis of 2,2'-Binaphthol-Type Biaryls under Mild Reaction Conditions
Mauro Moliterno1, Riccardo Cari1, Antonio Puglisi1
1Dipartimento di Chimica, Sapienza University of Roma, P. le Aldo Moro 5, 00185, Roma (I, Italy.
Abstract:
Simple quinine as an organocatalyst mediates the addition of various naphthols to halogenated quinones to afford non-C2 -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.
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