Efficient Synthesis of a C2-Symmetric 2,2'-Bipyridine-α,α'-1-t-butyl-diol Ligand by Stereoselective Double Hydrogen Transfer to a 2,2'-Bipyridine-diketone
- PMID: 39049430
- DOI: 10.1002/chem.202402449
Efficient Synthesis of a C2-Symmetric 2,2'-Bipyridine-α,α'-1-t-butyl-diol Ligand by Stereoselective Double Hydrogen Transfer to a 2,2'-Bipyridine-diketone
Abstract
An efficient and practical method was developed for the synthesis of C2-symmetric 2,2'-bipyridine-α,α'-1-t-butyl-diol ligands. The disclosed synthesis involves the Ullmann homocoupling of a keto bromo-pyridine under NiCl2/Zn/PPh3 conditions, followed by the stereoselective double hydrogen transfer to the obtained 2,2'-bipyridine-diketone using RuII Noyori-Ikariya catalysts. This approach allowed the successful synthesis of 2,2'-bipyridine-α,α'-1-t-butyl-diol, i.e (S,S)-Bolm's ligand, with a quantitative yield and an excellent stereoselectivity (ee>99.5 %, de>99.5 %), with an overall yield of 69 % from easily accessible starting materials.
Keywords: Asymmetric catalysis; Chiral ligand; Enantioselectivity; Hydrogen transfer; Noyori-Ikariya catalyst; Stereoselective reduction.
© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.
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