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Relevant academic research and scientific papers

Tuning the peri effect for enantioselectivity: Asymmetric hydrogenation of unfunctionalized olefins with the BIPI ligands

The modular nature of the BIPI ligands allows for systematic optimization of each ligand region. The development of ligands optimized for asymmetric hydrogenation of the challenging unfunctionalized olefin substrate class is described. The naphthyl peri p

Method for preparing chiral alkyl compound by catalyzing asymmetric hydrogenation reaction of olefin with iron complex catalyst

The invention discloses a method for preparing a chiral alkyl compound by catalyzing asymmetric hydrogenation reaction of olefin with an iron complex catalyst, which comprises the steps of by taking disubstituted olefin as shown in a formula I defined in

Monohydride-Dichloro Rhodium(III) Complexes with Chiral Diphosphine Ligands as Catalysts for Asymmetric Hydrogenation of Olefinic Substrates

We report full details of the synthesis and characterization of monohydride-dichloro rhodium(III) complexes bearing chiral diphosphine ligands, such as (S)-BINAP, (S)-DM-SEGPHOS, and (S)-DTBM-SEGPHOS, producing cationic triply chloride bridged dinuclear rhodium(III) complexes (1 a: (S)-BINAP; 1 b: (S)-DM-SEGPHOS) and a neutral mononuclear monohydride-dichloro rhodium(III) complex (1 c: (S)-DTBM-SEGPHOS) in high yield and high purity. Their solid state structure and solution behavior were determined by crystallographic studies as well as full spectral data, including DOSY NMR spectroscopy. Among these three complexes, 1 c has a rigid pocket surrounded by two chloride atoms bound to the rhodium atom together with one tBu group of (S)-DTBM-SEGPHOS for fitting to simple olefins without any coordinating functional groups. Complex 1 c exhibited superior catalytic activity and enantioselectivity for asymmetric hydrogenation of exo-olefins and olefinic substrates. The catalytic activity of 1 c was compared with that of well-demonstrated dihydride species derived in situ from rhodium(I) precursors such as [Rh(cod)Cl]2 and [Rh(cod)2]+[BF4]? upon mixing with (S)-DTBM-SEGPHOS under dihydrogen.

Tetrahydroquinoline skeleton chiral phosphine-nitrogen ligand and preparation method and application thereof

The invention relates to the field of asymmetric catalytic hydrogenation, in particular to a tetrahydroquinoline skeleton chiral phosphine-nitrogen ligand and a preparation method and application thereof. The tetrahydroquinoline skeleton chiral phosphine-

Improved synthesis of cyclohexane-backbone iridium-complexes of quinoline-phosphine and their applications in asymmetric hydrogenation

– The iridium-complexes 3 and 4 with cyclohexane-backbone derived from quinoline were easily synthesized. The key step is cis/trans stereoselective reduction of 2-(quinolin-2-yl)cyclohexanone 5 to trans-2-(quinolin-2-yl)cyclohexanol 6 using Al(Oi-Pr)3/i-P

Tandem Peterson olefination and chemoselective asymmetric hydrogenation of β-hydroxy silanes

Here, we report the first Ir-N,P complex catalyzed tandem Peterson olefination and asymmetric hydrogenation of β-hydroxy silanes. This reaction resulted in the formation of chiral alkanes in high isolated yields (up to 99%) and excellent enantioselectivity (up to 99% ee) under mild conditions. Modification of the reaction conditions provides a choice to transform either an olefin or the β-hydroxy silane in a chemoselective manner. Additionally, based on this method, an expedient enantioselective synthesis of (S)-(+)-α-curcumene, from a simple ketone, was accomplished in two steps with 75% overall yield and 95% ee.

Ir/Thioether-Carbene, -Phosphinite, and -Phosphite Complexes for Asymmetric Hydrogenation. A Case for Comparison

We studied for the first time the potential of novel and simple Ir/thioether-NHC complexes in the asymmetric hydrogenation of unfunctionalized olefins and cyclic β-enamides. For comparison, we prepared and applied the analogues thioether-phosphinite/phosphite complexes. We found that the efficiency of the new Ir/thioether-NHC catalyst precursors varies with the type of olefin. Thus, while the Ir/thioether-NHC catalyst precursors provided lower catalytic performance than their related Ir/thioether-P complexes in the hydrogenation of olefins lacking a coordinating group, the catalysts had similar good performance for the reduction of functionalized olefins (e.g., tri- and disubstituted enol phosphonate derivatives). Catalytic results together with the studies of the reactivity toward H2 indicated that the thioether-carbene design favors the formation of inactive trinuclear species, which are responsible for the low activities obtained with these carbene-type catalysts. Nevertheless, this catalyst deactivation can be avoided by using functionalized olefins such as enol phosphonates. We also report the discovery of simple-to-synthesize Ir/thioether-P catalysts containing a simple backbone that gave high enantioselectivities for some trisubstituted olefins, some challenging 1,1′-disubstituted olefins, and cyclic β-enamides.

Enantioselective synthesis of tunable chiral pyridine-aminophosphine ligands and their applications in asymmetric hydrogenation

A small library of tunable chiral pyridine-aminophosphine ligands were enantioselectively synthesized based on chiral 2-(pyridin-2-yl)-substituted 1,2,3,4-tetrahydroquinoline scaffolds, which were obtained in high yields and with excellent enantioselectivities via ruthenium-catalyzed asymmetric hydrogenation of 2-(pyridin-2-yl)quinolines. The protocol features a wide substrate scope and mild reaction conditions, enabling scalable synthesis. These chiral P,N ligands were successfully applied in the Ir-catalyzed asymmetric hydrogenation of benchmark olefins and challenging seven-membered cyclic imines including benzazepines and benzodiazepines. Excellent enantio- and diastereoselectivity (up to 99% ee and >20:1 dr), and/or unprecedented chemoselectivity were obtained in the asymmetric hydrogenation of 2,4-diaryl-3H-benzo[b]azepines and 2,4-diaryl-3H-benzo[b][1,4]diazepines.

Asymmetric Hydrogenation of Disubstituted, Trisubstituted, and Tetrasubstituted Minimally Functionalized Olefins and Cyclic β-Enamides with Easily Accessible Ir-P,Oxazoline Catalysts

We have developed a family of Ir-P,oxazoline catalysts for asymmetric hydrogenation. These catalysts, with a simple modular architecture, have shown a high tolerance to the olefin geometry and substitution pattern, and to the presence of several neighboring polar groups. Thus, they were able to successfully hydrogenate disubstituted, trisubstituted, and tetrasubstituted minimally functionalized olefins (with enantiomeric excess values up to 99%). The excellent catalytic performance was also extended to the hydrogenation of cyclic β-enamides.

Pyrrolidine-Based P,O Ligands from Carbohydrates: Easily Accessible and Modular Ligands for the Ir-Catalyzed Asymmetric Hydrogenation of Minimally Functionalized Olefins

The potential of P,O-iminosugar based ligands in the Ir-catalyzed asymmetric hydrogenation of minimally functionalized olefins is presented. These new ligands were prepared from easily available carbohydrates (D-mannose, D-ribose and D-arabinose). The stereochemical and polyfunctional diversity of carbohydrates allowed the modulation of the ligands, both from their electronic properties and the rigidity of their backbone. High enantioselectivities (ee’s up to 99 %) can be reached in the hydrogenation of selected tri- and disubstituted substrates.