BINAP — The People′s Ligand for Chiral Chemistry

Strong, Jerry G.

doi:10.1002/chin.200430241

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Atropisomerism 21 Atropisomerism1

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2021

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“…In practical terms, for the isolation of enantiopure forms, the interconversion of atropisomers should exhibit a half-life of at least 1000 s at 300 K which corresponds to an energy barrier for rotation of 93 kJ mol −1 [25,26]. Inorganic chemists are probably most familiar with the phenomenon of atropisomerism in the context of chelating bisphosphane ligands such as BINAP ([1,1 -binaphthalene]-2,2 -diylbis(diphenylphosphane), 6, Figure 3a) [27][28][29][30][31][32][33][34][35]. It is instructive to use ligand 6 to illustrate the consequences of coordination.…”

Section: Atropisomerism 21 Atropisomerismmentioning

confidence: 99%

1,1′-Biisoquinolines—Neglected Ligands in the Heterocyclic Diimine Family That Provoke Stereochemical Reflections

2021

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1,1′-Biisoquinolines are a class of bidentate nitrogen donor ligands in the heterocyclic diimine family. This review briefly discusses their properties and the key synthetic pathways available and then concentrates upon their coordination behaviour. The ligands are of interest as they exhibit the phenomenon of atropisomerism (hindered rotation about the C1–C1′ bond). A notation for depicting the stereochemistry in coordination compounds containing multiple stereogenic centers is developed. The consequences of the chirality within the ligand on the coordination behaviour is discussed in detail.

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