138983-03-6Relevant articles and documents
Copper-catalyzed asymmetric reductions of aryl/heteroaryl ketones under mild aqueous micellar conditions
Etemadi-Davan, Elham,Fialho, David M.,Gadakh, Amol,Langner, Olivia C.,Lipshutz, Bruce H.,Sambasivam, Ganesh,Takale, Balaram S.
supporting information, p. 3282 - 3286 (2021/05/29)
Enantioselective syntheses of nonracemic secondary alcohols have been achieved in an aqueous micellar medium via copper-catalyzed (Cu(OAc)2·H2O/(R)-3,4,5-MeO-MeO-BIPHEP) reduction of aryl/heteroaryl ketones. This methodology serves as a green protocol to access enantio-enriched alcohols under mild conditions (0-22 °C) using a base metal catalyst, together with an inexpensive, innocuous, and convenient stoichiometric hydride source (PMHS). The secondary alcohol products are formed in good to excellent yields with ee values greater than 90%.
Preparation of new chiral pyridine-phosphine ligands and their Pd-catalyzed asymmetric allylic alkylations
Uenishi, Jun'ichi,Hamada, Masahiro
, p. 2999 - 3006 (2007/10/03)
Enantiomerically pure 2-(diphenylphosphino)methyl-N-[1-(2-pyridinyl)ethyl] 1 and 2 have been prepared by the stereospecific substitution of enantiomerically pure 1-(2-pyridinyl)ethyl methanesulfonate 6 eith enantiomerically pure 2-(diphenylphosphino)methylpyrrolidine. Asymmetric allylic akylation of 1,3-diphenyl-2-propenyl acatate 11 with dimethyl malonate sodium salt using the (S,S)-ligand 1 affords the (R)-product 12 with up to 86% e.e. in good yield.
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