Quinine‐Catalyzed Asymmetric Synthesis of 2, 2′‐Binaphthol‐Type Biaryls under Mild Reaction Conditions. Issue 22 (20th April 2016)

• Record Type: Journal Article
• Authors: Moliterno, Mauro; Cari, Riccardo; Puglisi, Antonio; Antenucci, Achille; Sperandio, Céline; Moretti, Erica; Di Sabato, Antonio; Salvio, Riccardo; Bella, Marco
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 22(2016)
• Page Start: 6525
• Page End: 6529
• Publication Date: 2016-04-20
• Subjects: atropisomers -- biaryls -- chirality -- density-functional calculations -- organocatalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201601660
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Simple is better : Commercially available reagents such as quinones and naphthols are combined under mild reaction conditions in the presence of quinine to afford halogenated 2, 2′‐binaphthol‐like biaryls in gram quantities. The products are isolated in good yield and stereoselectivity.