137848-29-4Relevant articles and documents
Synthesis of new BINAP-based aminophosphines and their 31P-NMR spectroscopy
Anstiss, Christopher,Karuso, Peter,Richardson, Mark,Liu, Fei
, p. 2788 - 2802 (2013)
BINAP aminophosphines are prevalent N,P-bidentate, chiral ligands for asymmetric catalysis. While modification via the BINAP-nitrogen linkage is well explored and has provided a diverse body of derivatives, modification of the other substituents of the phosphorous center is another avenue in generating new congeners of this important class of chiral ligands. Herein reported are new BINAP aryl aminophosphines with electron rich or deficient substituents on the aryl rings. This scalable synthesis converted readily available starting material, (S)-BINOL, to a key intermediate (S)-NOBIN, from which the final chiral aminophosphines were prepared via a palladium-catalyzed, phosphonylation reaction. The aryl substituents are able to modify the electronic properties of the phosphorous center as indicated by the range of 31P-NMR shifts of these new ligands. A computational analysis was performed to linearly quantitate contributions to the 31P-NMR shifts from both resonance and field effects of the substituents. This correlation may be useful for designing and preparing other related aminophosphines with varying ligand properties.
Synthesis and optical properties of (S)-Nobin
Studentsov,Piskunova,Skvortsov,Skvortsov
, p. 962 - 966 (2009)
A preparative method of synthesis of optically pure S-2-amino-2'-hydroxy-1, 1'-binaphthyl (S-Nobin), the precoursor in the synthesis of other asymmetric 1,1-binaphthyls applied as the ligands at the creation of the catalysts of asymmetric synthesis, is mo
Enantioselective catalysis. Part 143: Astonishingly high enantioselectivity in the transfer hydrogenation of acetophenone with 2-propanol using Ru complexes of the Schiff base derived from (S)-2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) and 2-pyridinecarbaldehyde
Brunner, Henri,Henning, Frauke,Weber, Matthias
, p. 37 - 42 (2002)
A series of bidentate and tridentate (S)-NOBIN derivatives was synthesised and tested as chiral ligands in the Ru-catalysed enantioselective transfer hydrogenation of acetophenone with 2-propanol. Despite the similarities in chemical structure, only the imine derived from (S)-NOBIN and 2-pyridinecarbaldehyde and the corresponding amine (obtained by NaBH4 reduction of the imine) afforded (S)-1-phenylethanol in nearly quantitative yields and outstanding enantioselectivities of up to 97% e.e.
A Chiral Iron Disulfonate Catalyst for the Enantioselective Synthesis of 2-Amino-2′-hydroxy-1,1′-binaphthyls (NOBINs)
Dyadyuk, Alina,More, Nagnath Yadav,Pappo, Doron,Shalev, Hen,Shalit, Hadas,Vershinin, Vlada
supporting information, p. 3676 - 3684 (2022/03/02)
A novel type of chiral redox disulfonate iron complex for asymmetric catalysis is reported. The [Fe((Ra)-BINSate)]+(BINSate = 1,1′-binaphthalene-2,2′-disulfonate) complex effectively promotes the enantioselective oxidative cross-coupling between 2-naphthols (1) and 2-aminonaphthalene derivatives (2), affording optically enriched (Ra)-2-amino-2′-hydroxy-1,1′-binaphthyls (NOBINs) with exceptional yields and enantioselective ratios (up to 99% yield and 96:4 er). The [Fe((Ra)-BINSate)]+catalyst was designed as a chiral version of FeCl3with multicoordination sites available for binding the two coupling partners 1 and 2 as well as the oxidant. Our structure-selectivity and activity study, which covered most of the important positions in the NOBIN scaffold, revealed the effect of different substitution patterns on the coupling efficiency and stereoselectivity.
Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction
Chen, Yuan,Fang, Siqiang,Pan, Jianke,Ren, Xiaoyu,Tan, Jian-Ping,Wang, Tianli,Zhang, Hongkui
, p. 14921 - 14930 (2021/05/10)
A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.
