Abstract
One pathway for the preparation of enantiomerically pure compounds from prochiral substrates is the use of metal complex catalysis with chiral ligands. Compared to the other frequently used chiral ligands, chiral 2,2′-bipyridines have been underexploited, despite the data indicating that such ligands have considerable potential in synthetic chemistry. One of those is the so-called Bolm’s ligand, a compound possessing chiral alcohol moieties in the side chains attached to the 2,2′-bipyridine scaffold. Various metal salts have been used in combination with Bolm’s ligand as potent catalysts able to bring about enantioselective alkylations, allylations, conjugate additions, desymmetrization of meso-epoxides, aldol reactions, etc. This review aims to summarize Bolm’s ligand applications in the area of enantioselective synthesis over the last three decades since its preparation.
Highlights
Growing demands for chiral compounds in pharmaceutical, agrochemical, and other fields of chemical industry have resulted in the search for new, more selective, economical, and environmentally friendly approaches in asymmetric synthesis
Enantioselective catalysis by means of chiral metal complexes is one such approach. Endeavors in this field are closely associated with the development of new chiral ligands that are able to modulate the reactivity of the metal center in such a way that the prochiral compound is selectively transformed into one out of two possible enantiomers
In comparison to other classes of chiral ligands based on phosphines, salens, oxazolines, or the tartrate scaffolds, chiral 2,20 -bipyridines have attracted comparatively little attention
Summary
Growing demands for chiral compounds in pharmaceutical, agrochemical, and other fields of chemical industry have resulted in the search for new, more selective, economical, and environmentally friendly approaches in asymmetric synthesis In this respect, enantioselective catalysis by means of chiral metal complexes is one such approach. 2020, 25, 958 thanks eight carbon atoms, the changewhich of steric and electronic properties, achievement substituents increase stericto hindrance, hampers the accessibility of enables the twothe nitrogen atoms of the optimal behaviorOn of the other wholehand, complex for the appropriate application [7].capable of chelation towards coordination. The substitution of the 2,20 -bipyridine scaffold in the positions 6 and 60 causes the most significant significant changes1).in the coordination abilities ofchain the bearing corresponding bipyridine. The most frequently used chiral 2,2’-bipyridine ligand, and perhaps the most versatile one used
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