127049-52-9Relevant academic research and scientific papers
Synthesis of a Bolm's 2,2′-Bipyridine Ligand Analogue and Its Applications
Bedná?ová, Eva,Dra?ínsky, Martin,Malatinec, ?tefan,Císa?ová, Ivana,Lamaty, Frédéric,Kotora, Martin
, p. 2869 - 2878 (2018/08/17)
A new method of synthesis of an analogue of Bolm's 2,2′-bipyridine ligand based on the catalytic [2+2+2] cyclotrimerization of 1-halodiynes with nitriles was developed. Crucial step of the whole synthesis turned out to be homodimerization of a substituted 2-bromopyridine to the corresponding bipyridine, that was studied and optimized. The newly prepared bipyridine (S,S)-2 was then tested as a chiral ligand in metal-catalyzed enantioselective reactions. Out of the studied reactions the most promising results were obtained in epoxide ring opening (82% yield, 98% ee) and Mukaiyama aldol reaction (>96% yield, 99/1 dr, 92% ee). In the case of Mukaiyama-aldol reaction as well as in the Michael addition, novel ligand 2 proved its robustness compared to Bolm's ligand as it was less sensitive to the purity of used reagents. (Figure presented.).
Optically pure bulky (hetero)arylalkyl carbinols via kinetic resolution
Hu, Bin,Meng, Meng,Fossey, John S.,Mo, Weimin,Hu, Xinquan,Deng, Wei-Ping
scheme or table, p. 10632 - 10634 (2011/10/30)
Planar chiral nucleophilic catalyst Fc-PIP was employed in the kinetic resolution of bulky (hetero)arylalkyl carbinols delivering unreacted alcohols with extremely high enantiomeric excess (>99.0% ees) in ideal conversions ranging from 50.4-56.7%.
New efficient method for the synthesis of chiral 2,2′-bipyridyl ligands
Ishikawa, Shunpei,Hamada, Tomoaki,Manabe, Kei,Kobayashi, Shu
, p. 2176 - 2182 (2007/10/03)
An efficient preparation of chiral 2,2′-bipyridines was developed. Compound 1 was synthesized in 54% yield for three steps starting from 2,6-dibromopyridine. In this synthesis, only catalytic amounts of metals were used in the asymmetric reduction and homo-coupling reaction steps. The total yield and simplicity of experimental procedures were much improved compared with those of the previous report. Other chiral 2,2′-bipyridines were similarly synthesized with high efficiency. Georg Thieme Verlag Stuttgart.
Enantioselective Synthesis of Optically Active Pyridine Derivatives and C2-Symmetric 2,2'-Bipyridines
Bolm, Carsten,Ewald, Martina,Felder, Marcel,Schlingloff, Gunther
, p. 1169 - 1190 (2007/10/02)
Optically active pyridine derivatives 2, 15, 18, 19, 21, 26, and 27 are obtained by enantioselective reduction of the corresponding ketones 5, 7, 11-13, 24, and 25 using the chiral borane reagent chlorodiisopinocampherylborane .Nickel(0)-mediated coupling of bromopyridines 2, 15, and 31 gives C2-symmetric 2,2'-bipyridines (R,R)-32, (R,R)-33, and (S,S)-38, respectively, which form metal complexex with Co(II), Pd(II), Cu(I), and Ag(I).Aryl-substituted pyridines 26, and 39-41 are synthesized by palladium(0)-catalized cross coupling of 2 and 15 with boronic acids 42-44.Key Words: 2,2-Bipyridines / Pyridines, optically active / Chiral ligands / Asymmetric Synthesis / Catalysis, enantioselective
