141478-36-6Relevant articles and documents
“Backdoor Induction” of Chirality: Trans-1,2-cyclohexanediamine as Key Building Block for Asymmetric Hydrogenation Catalysts
Glasovac, Zoran,Kirin, Sre?ko I.,Kokan, Zoran,Opa?ak, Sa?a,Peri?, Berislav
, p. 2115 - 2128 (2019)
This paper describes the synthesis and characterization of 21 chiral monodentate ligands L, assembled of three building blocks utilizing amide bonds: a metal binding triphenylphosphine, a chiral cyclic diamine and an additional substituent for fine-tuning the steric and/or electronic properties. Cis square-planar metal complexes of RhI and PtII with ML2 stoichiometry have been prepared and characterized by spectroscopic methods (NMR, IR, UV-Vis, CD) and DFT calculations. A key feature of the metal complexes is a prochiral metal coordination sphere and “backdoor induction” of chirality from a distant chiral source via an outer-coordination sphere, well-defined by aromatic stacking and hydrogen-bonding. The rhodium complexes were used as catalysts in asymmetric hydrogenation of α,β-dehydroamino acids with excellent yield and selectivity (up to 97 % ee), strongly supporting the “backdoor induction” hypothesis.
Asymmetric conjugate addition of α,α-disubstituted aldehydes to nitroalkenes organocatalyzed by chiral monosalicylamides from trans-cyclohexane-1,2-Diamines
Martínez-Guillén, José R.,Flores-Ferrándiz, Jesús,Gómez, Cecilia,Gómez-Bengoa, Enrique,Chinchilla, Rafael
, (2018/01/18)
Primary amine-salicylamides derived from chiral trans-cyclohexane-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to arylated and heteroarylated nitroalkenes. The reaction is performed in
CDI-mediated monoacylation of symmetrical diamines and selective acylation of primary amines of unsymmetrical diamines
Verma, Sanjeev K.,Ghorpade, Ramarao,Pratap, Ajay,Kaushik
, p. 326 - 329 (2012/04/10)
A highly efficient and green protocol for monoacylation of symmetrical diamines and chemoselective acylation of primary amines of unsymmetrical diamines has been developed.