Quinine‐Catalyzed Asymmetric Synthesis of 2,2′‐Binaphthol‐Type Biaryls under Mild Reaction Conditions |
| |
| Authors: | Mauro Moliterno Riccardo Cari Antonio Puglisi Achille Antenucci Céline Sperandio Erica Moretti Antonio Di?Sabato Dr Riccardo Salvio Prof Marco Bella |
| |
| Affiliation: | 1. Dipartimento di Chimica, Sapienza University of Roma, Roma (I, Italy;2. IMC-CNR Sezione Meccanismi di Reazione, Università di Roma—Sapienza, Roma, 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. |
| |
| Keywords: | atropisomers biaryls chirality density-functional calculations organocatalysis |
|
|
