Asymmetric Hydrogenation of Aromatic Olefins Catalyzed by Iridium Complexes of Proline-Derived Phosphine—Oxazoline Ligands.

ChemInform ◽  
2003 ◽  
Vol 34 (18) ◽  
Author(s):  
Guopin Xu ◽  
Scott R. Gilbertson
Keyword(s):  
Asymmetric Hydrogenation ◽  
Iridium Complexes ◽  
Oxazoline Ligands

Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin via iridium-catalyzed asymmetric hydrogenation

2021 ◽  
Vol 57 (2) ◽  
pp. 195-198
Author(s):  
Xiang-Yu Ye ◽  
Zhi-Qin Liang ◽  
Cong Jin ◽  
Qi-Wei Lang ◽  
Gen-Qiang Chen ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Hydrogenation ◽  
High Reactivity ◽  
Iridium Complexes ◽  
Oxazoline Ligands

A series of highly rigid oxa-spiro phosphine–oxazoline ligands (O-SIPHOX) were synthesized efficiently, their iridium complexes showed high reactivity and enantioselectivity in the synthesis of key intermediate of anti-obesity drug lorcaserin.

Iridium Complexes with Phosphine−Phosphite Ligands. Structural Aspects and Application in the Catalytic Asymmetric Hydrogenation of N-Aryl Imines

2006 ◽  
Vol 25 (4) ◽  
pp. 961-973 ◽  
Author(s):  
Sergio Vargas ◽  
Miguel Rubio ◽  
Andrés Suárez ◽  
Diego del Río ◽  
Eleuterio Álvarez ◽  
...  
Keyword(s):  
Asymmetric Hydrogenation ◽  
Iridium Complexes ◽  
Phosphite Ligands ◽  
Catalytic Asymmetric ◽  
Catalytic Asymmetric Hydrogenation ◽  
Structural Aspects

ChemInform Abstract: Iridium-Catalyzed Asymmetric Hydrogenation of Olefins Using TIQ Phosphine-Oxazoline Ligands.

ChemInform ◽  
2011 ◽  
Vol 42 (7) ◽  
pp. no-no
Author(s):  
Sai Kumar Chakka ◽  
Byron K. Peters ◽  
Pher G. Andersson ◽  
Glenn E. M. Maguire ◽  
Hendrik G. Kruger ◽  
...  
Keyword(s):  
Asymmetric Hydrogenation ◽  
Oxazoline Ligands

ChemInform Abstract: Asymmetric Hydrogenation of Quinolines Catalyzed by Iridium Complexes of Monodentate BINOL-Derived Phosphoramidites.

ChemInform ◽  
2008 ◽  
Vol 39 (39) ◽  
Author(s):  
Natasa Mrsic ◽  
Laurent Lefort ◽  
Jeroen A. F. Boogers ◽  
Adriaan J. Minnaard ◽  
Ben L. Feringa ◽  
...  
Keyword(s):  
Asymmetric Hydrogenation ◽  
Iridium Complexes

Temperature-Controlled Bidirectional Enantioselectivity in Asymmetric Hydrogenation Reactions Utilizing Stereodynamic Iridium Complexes

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3485-3494 ◽  
Author(s):  
Max Siebert ◽  
Golo Storch ◽  
Frank Rominger ◽  
Oliver Trapp
Keyword(s):  
Elevated Temperatures ◽  
Asymmetric Hydrogenation ◽  
Iridium Complexes ◽  
Chirality Transfer ◽  
Iridium Catalysts ◽  
Thermal Equilibration ◽  
Hydrogenation Reactions ◽  
Temperature Controlled ◽  
First Time ◽  
Solid State Structures

Stereochemically flexible 2,2(-bis(diphenylphosphino)biphenyl (BIPHEP) ligands were modified with chiral α-substituted carboxylic acid auxiliaries in the 3- and 3′-position. The resulting central-to-axial chirality transfer to the stereochemically flexible chiral axis of the BIPHEP­ core was investigated as well as complexation of these diastereomeric ligands to iridium(I). Solid-state structures of both ligand diastereomers and a diastereomerically pure iridium(I) BIPHEP complex were obtained. Thermal equilibration of the resulting iridium(I) complexes was studied to investigate the stereodynamic properties of the BIPHEP ligands. The iridium(I) complexes without and after pre-catalysis warming in solution — which induces a shift of the diastereomeric ratio — were applied for asymmetric hydrogenation of a prochiral α-substituted acrylic acid, resulting in temperature-controlled bidirectional enantioselectivity of iridium catalysts for the first time. In both cases, enantioenriched (R)-naproxen as well as (S)-naproxen — after re-equilibration of the catalyst at elevated temperatures — was obtained by using the same catalyst.

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