Spontaneous transfer of chirality in an atropisomerically enriched two-axis system. Enantioselective synthesis of multisubstituted biaryl skeleton by chiral phosphoric acid catalysed desymmetrization/kinetic resolution sequence. Dynamic kinetic resolution of biaryl atropisomers via peptide-catalysed asymmetric bromination. Nonbiaryl and heterobiaryl atropisomers: molecular templates with promise for atropselective chemical transformations. Kumarasamy, E., Raghunathan, R., Sibi, M. Organocatalytic aryl–aryl bond formation: an atroposelective -rearrangement approach to BINAM dericatives. Catalytic asymmetric benzidine rearrangement. Preparation of 2-amino-2′-hydroxy-1,1′-binaphthyl and N-arylated 2-amino-1,1′-binaphthyl derivatives via palladium-catalyzed amination. Organocatalytic asymmetric arylation of indoles enabled by azo groups. A facile synthesis of 2,2′,3-trisubstituted and 2,2′,3,3′-tetrasubstituted 1,1′-binaphthyls. Selective cross-coupling of 2-naphthol and 2-naphthamine derivatives. A facile synthesis of 2-amino-2′-hydroxy-1,1′-binaphthyl and 2,2′-diamino-1,1′-binaphthyl by oxidative coupling using copper ( ii) chloride. Two stereoinduction events in one C–H activation step: a route towards terphenyl ligands with two atropisomeric axes. Aromatic C–H coupling with hindered arylboronic acids by Pd/Fe dual catalysts. Hindered biaryls by C–H coupling: bisoxazoline-Pd catalysis leading to enantioselective C–H coupling. Yamaguchi, K., Yamaguchi, J., Studerb, A. Catalyst-controlled stereoselective synthesis of atropisomers. Synthesis of axially chiral biaryl compounds by asymmetric catalytic reactions with transition metals. Loxq, P., Manoury, E., Poli, R., Deydier, E. Palladium catalyzed asymmetric Suzuki–Miyaura coupling reactions to axially chiral biaryl compounds: chiral ligands and recent advances. Recent advances and new concepts for the synthesis of axially stereoenriched biaryls. Wencel-Delord, J., Panossian, A., Leroux, F. Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling. Ten years of research on NOBIN chemistry. Synthesis of NOBIN derivatives for asymmetric catalysis. Modified BINOL ligands in asymmetric catalysis. Non-symmetrically substituted 1,1′-binaphthyls in enantioselective catalysis. 1,1′-Binaphthyl dimers, oligomers, and polymers: molecular recognition, asymmetric catalysis, and new materials. BINAP: an efficient chiral element for asymmetric catalysis. Interlocked chiral nanotubes assembled from quintuple helices. Towards chiral microporous soluble polymers-binaphthalene-based polyimides. Binaphthyl-bipyridyl cyclic dyads as a chiroptical switch. Reversible photoswitchable axially chiral dopants with high helical twisting power. Li, Q., Green, L., Venkataraman, N., Shiyanovskaya, I. Total chromatographic optical resolution of α-amino acid and ester salts through chiral recognition by a host covalently bound to polystyrene resin. Enantioselective fluorescent sensors: a tale of BINOL. Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Atroposelective total synthesis of axially chiral biaryl natural products. This work provides an alternative avenue to enantioenriched biaryls, and provides the capability to explore the synthetic and catalytic potentials of NOBIN- and BINAM-based frameworks.īringmann, G., Gulder, T., Gulder, T. Two complementary systems were devised employing a chiral phosphoric acid–salt complex or Ni(OTf) 2/chiral bis(oxazoline) ligand catalytic system for accessing atropisomeric NOBIN and BINAM derivatives, respectively. Here, we report a method for the asymmetric synthesis of a myriad of 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) and 1,1’-binaphthyl-2,2’-diamine (BINAM) derivatives in excellent yields and enantioselectivities via a redox-neutral cross-coupling protocol. However, their development is hindered due to the lack of convenient and pragmatic protocols. Enantioselective aryl–aryl cross-coupling provides the most straightforward entry to atropisomeric biaryls, with remarkable application potential in the field of chemical science. Atropisomerically enriched biaryl frameworks are ubiquitous in many fields of chemistry.
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