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Relevant academic research and scientific papers

A diastereomeric pair of sulfoxide-containing chiral MOP-type ligands: Preparation and application to rhodium-catalyzed asymmetric 1,4-addition reactions

(R,SS)-Sulfoxide-MOP (L2) and (R,RS)-sulfoxide-MOP (L3) were developed as a diastereomeric pair of sulfoxide-containing chiral MOP-type ligands. These two ligands also represent the first monosulfoxide analogues of BINAP. The chiral ligand L2 was successfully applied to the highly enantioselective rhodium-catalyzed 1,4-addition between α,β-unsaturated ketones or esters and arylboronic acids, and exhibited a broad substrate scope when the reaction was performed using 1.5 mol% Rh in cyclohexane/H2O (10:1) at 40 °C under mild basic conditions.

Allenylic Carbonates in Enantioselective Iridium-Catalyzed Alkylations

An enantioconvergent C(sp3)-C(sp3) coupling between racemic allenylic electrophiles and alkylzinc reagents has been developed. An Ir/(phosphoramidite,olefin) catalyst provides access to highly enantioenriched allenylic substitution p

Role of Regioisomeric Bicyclo[3.3.0]octa-2,5-diene Ligands in Rh Catalysis: Synthesis, Structural Analysis, Theoretical Study, and Application in Asymmetric 1,2- and 1,4-Additions

In order to study the impact of regioisomeric diene ligands on the formation and catalytic activity of Rh complexes, a series of C2- and CS-symmetric 2,5-disubstituted bicyclo[3.3.0]octa-2,5-dienes C2-L and CS-L, respectively, were synthesized from Weiss diketone by simultaneous deprotonation/electrophilic trapping of both oxo functions, and the catalytic behavior was studied in the presence of [RhCl(C2H4)2]2. Complexes [RhCl(C2-L)]2 bearing C2-symmetric ligands catalyzed effectively the asymmetric arylation of N-tosylaldimines to (S)-diarylamines with yields and ee values up to 99%. In Hayashi-Miyaura reactions, however, the complexes showed poor catalytic activity. When complexes [RhCl(CS-L)]2 with CS-symmetric ligand or mixtures of [RhCl(C2-L)]2 and [RhCl(CS-L)]2 were employed in 1,2-additions, racemic addition products were observed, suggesting a C=C isomerization of the diene ligands. X-ray crystal structure analysis of both Rh complexes formed from the [RhCl(C2H4)2]2 precursor and ligands C2-L and CS-L revealed that only the C2-symmetric ligand C2-L coordinated to the Rh, whereas CS-L underwent a Rh-catalyzed C=C isomerization to rac-C2-L, which then gave the racemic [RhCl(rac-C2-L)]2 complex. DFT calculations of the relative stabilities of the Rh complexes and the proposed intermediates provided a mechanistic rationale via Rh-mediated hydride transfer.

PHOSPHINE-OLEFIN LIGAND HAVING FACE ASYMMETRIC CYCLOPENTADIENYL-MANGANESE COMPLEX IN BASIC SKELETON

PROBLEM TO BE SOLVED: To provide a face asymmetric ligand for a transition metal catalyst asymmetric reaction high in yield and optical purity to not only a cyclic enone compound, but also various enone compounds containing an aliphatic enone compound. SO

Phosphine-olefin ligands based on a planar-chiral (π-Arene)chromium scaffold: Design, synthesis, and application in asymmetric catalysis

The NMR and X-ray crystallographic studies clarified that planar-chiral alkenylene-bridged (phosphino-π-arene)(phosphine)chromium complexes 3 were capable of coordinating to a rhodium(I) cation in a bidentate fashion at the (π-arene)-bound phosphorus atom

Chiral bicyclic [2.2.2] octadiene ligands for Rh-catalysed catalytic asymmetric conjugate additions to acyclic enones: A quantitative structure-property relationship

A series of chiral bicyclic [2.2.2]diene ligands gave variable ee values for Rh-catalysed asymmetric conjugate addition to an acyclic enone. The interplay between electronic and steric effects was captured in a robust predictive quantitative structure-property relationship (QSPR) model for enantioselectivity. The Royal Society of Chemistry 2012.

(S)-Phenylalanine-derived chiral phosphorus-olefin ligands in rhodium-catalyzed asymmetric 1,4-addition reactions

Chiral phosphorus-olefins (S)-1, (S)-4, and (S)-5 have been designed and synthesized. These ligands were all synthesized from (S)-phenylalanine derivatives and act as phosphorus-olefin bidentate ligands to rhodium. The coordination face of the olefin can

Rhodium-catalyzed asymmetric 1,4-additions, in water at room temperature, with in-flask catalyst recycling

Using the newly introduced designer surfactant polyethylene glycol ubiquinol sebacate (PQS), as the platform for micellar catalysis, non-racemic BINAP has been covalently attached and rhodium(I) inserted to form PQS-BINAP-Rh. This species, the first examp

Polymer-incarcerated chiral Rh/Ag nanoparticles for asymmetric 1,4-addition reactions of arylboronic acids to enones: Remarkable effects of bimetallic structure on activity and metal leaching

Robust and highly active bimetallic Rh nanoparticle (NP) catalysts, PI/CB Rh/Ag, have been developed and applied to the asymmetric 1,4-addition of arylboronic acids to enones without leaching of the metals. We found that the structures of the bimetallic Rh/Ag catalysts and chiral ligands strongly affect their catalytic activity and the amount of metal leaching. PI/CB Rh/Ag could be recycled several times by simple operations while keeping high yields and excellent enantioselectivities. To show the versatility of the PI/CB Rh/Ag catalyst, a one-pot, oxidation-asymmetric 1,4-addition reaction of an allyl alcohol and an arylboronic acid was demonstrated by combining the PI/CB Rh/Ag catalyst with PI/CB Au as an aerobic oxidation catalyst.

(R)-3,5-diCF3-SYNPHOS and (R)- p -CF3-SYNPHOS, electron-poor diphosphines for efficient room temperature Rh-catalyzed asymmetric conjugate addition of arylboronic acids

Two new atropisomeric electron-poor chiral diphosphine ligand analogues of SYNPHOS were prepared, and their electronic properties are described. These two ligands afforded high performance for the Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds at room temperature.