99439-78-8

Upstream product

• 20826-80-6 2-phenylhex-1-ene 
• 28591-23-3 (+)(S)-6-bromo-2-phenyl-hexane 
• 22800-20-0 (-)-R-5-Phenylhexansaeure 
• 36617-83-1 (-)-R-N,N-Dimethyl-5-phenylhexanamid 
• 36617-86-4 (-)-R-N,N-Dimethyl-5-phenylhexylamin 
• 27798-98-7 (-)(R)-4-bromo-2-phenyl-butane 
• 2031-46-1 (R)-3-phenylbutanol 
• 772-14-5 (R)-3-phenylbutyric acid 
• 36617-92-2 (-)-R-5-Phenyl-1-hexen 

Downstream Products

• 66553-51-3 (-)(S)-2-cyclohexyl-hexane 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure allenes with central and axial chirality mediated by a remote sulfinyl group

Enantiomerically pure 2-(p-tolylsulfinyl)benzylcopper reagents react with propargyl bromides and mesylates, affording enantiomerically pure allenes with central and axial chirality. Both regioselectivity (SN2 processes) and configuration at the

Diphenylamine-amine-oxazoline ligand, synthesis method as well as metal complex and application thereof

The invention provides a diphenylamine-amine-oxazoline ligand which is a compound of formula (1) or an antipode or racemate of the compound of formula (1), wherein R1 and R2 are respectively and separately one of C1 to C10 hydrocarbon group, benzyl group, phenyl group or substituted phenyl group and heteroaryl group; and R3 is H or methyl. The invention also discloses a synthesis method as well asa metal complex and application thereof, which aims at providing a catalyst capable of realizing high synthesis yield by virtue of a simple synthesis route, and ensuring that the catalyst has very high catalytic activity in asymmetric hydrogenation and hydrogen transfer reactions of olefins and ketones.

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.

Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes

Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench-stable chiral oxazoline iminopyridine-cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral 1,1-diarylethanes. This process can be successfully performed under 1 atm of hydrogen at room temperature on gram scale.

Extending the substrate scope of bicyclic p-oxazoline/thiazole ligands for ir-catalyzed hydrogenation of unfunctionalized olefins by introducing a biaryl phosphoroamidite group

This study identifies a series of Ir-bicyclic phosphoroamidite-oxazoline/thiazole catalytic systems that can hydrogenate a wide range of minimally functionalized olefins (including E- and Z-tri- and disubstituted substrates, vinylsilanes, enol phosphinates, tri- and disubstituted alkenylboronic esters, and ?±,?2-unsaturated enones) in high enantioselectivities (ee values up to 99%) and conversions. The design of the new phosphoroamidite-oxazoline/thiazole ligands derives from a previous successful generation of bicyclic N-phosphane-oxazoline/thiazole ligands, by replacing the N-phosphane group with a p-acceptor biaryl phosphoroamidite moiety. A small but structurally important family of Ir-phosphoroamidite-oxazoline/thiazole precatalysts has thus been synthesized by changing the nature of the Ndonor group (either oxazoline or thiazole) and the configuration at the biaryl phosphoroamidite moiety. The substitution of the N-phosphane by a phosphoroamidite group in the bicyclic N-phosphane-oxazoline/thiazole ligands extended the range of olefins that can be successfully hydrogenated.

A modular furanoside thioether-phosphite/phosphinite/ phosphine ligand library for asymmetric iridium-catalyzed hydrogenation of minimally functionalized olefins: Scope and limitations

A highly modular furanoside thioether-phosphite/phosphinite/phosphine ligand library has been synthesized for the iridium-catalyzed asymmetric hydrogenation of minimally functionalized olefins. These ligands can be prepared efficiently from easily accessible D-(+)-xylose. We found that their effectiveness at transferring the chiral information in the product can be tuned by correctly choosing the ligand components. Enantioselectivities were therefore excellent (ees up to 99%) in a wide range of E- and Z-trisubstituted alkenes using 5-deoxyribofuranoside thioether-phosphite ligands. It should be pointed out that these catalysts are also very tolerant to the presence of a neighbouring polar group. For 1,1-disubstituted substrates, both enantiomers of the hydrogenation product can be obtained in high enantioselectivities simply by changing the configuration of the biaryl phosphite moiety. The asymmetric hydrogenation was also performed using propylene carbonate as solvent, which allowed the iridium catalysts to be reused while maintaining the excellent enantioselectivities. Copyright

A phosphite-pyridine/iridium complex library as highly selective catalysts for the hydrogenation of minimally functionalized olefins

A modular library of readily available phosphite-pyridine ligands has been successfully applied for the first time in the iridium-catalyzed asymmetric hydrogenation of a broad range of minimally functionalized olefins. The modular ligand design has been shown to be crucial in finding highly selective catalytic systems for each substrate. Excellent enantioselectivities (ees up to 99%) have therefore been obtained in a wide range of E- and Z-trisubstituted alkenes, including more demanding triaryl-substituted olefins and dihydronaphthalenes. This good performance extends to the very challenging class of terminal disubstituted olefins, and to olefins containing neighbouring polar groups (ees up to 99%). Both enantiomers of the reduction product can be obtained in excellent enantioselectivities by simply changing the configuration of the carbon next to the phosphite moiety. The hydrogenations were also performed using propylene carbonate as solvent, which allowed the iridium catalyst to be reused and maintained the excellent Copyright

Expanded scope of the asymmetric hydrogenation of minimally functionalized olefins catalyzed by iridium complexes with phosphite-thiazoline ligands

We have replaced the oxazoline group with a thiazoline moiety in one of the most successful of the phosphite-oxazoline ligand families for the Ir-catalyzed hydrogenation of minimally functionalized olefins. A small but structurally important library of Ir phosphite-thiazoline precatalysts (Ir-L1-L2a-e) has been developed by changing the substituents/configurations at the biaryl phosphite group. We found that the replacement of the oxazoline with a thiazoline moiety in the ligand design is beneficial in terms of substrate scope.

The application of pyranoside phosphite-pyridine ligands to enantioselective Ir-catalyzed hydrogenations of highly unfunctionalized olefins

Eight (biaryl)phosphite/pyridine ligands 1-2a-d have been prepared by the modular functionalization of positions C-2 and C-3 of two d-glucopyranoside backbones. The chiral ligands were examined in the iridium-catalyzed asymmetric hydrogenation of poorly functionalized alkenes, as a function of the relative position of the coordinating groups and the geometric properties of the biaryl phosphite moieties. Enantiomeric excesses of up to 90% were achieved in the hydrogenation of E-2-(4-methoxyphenyl)-2-butene by using 1a and 1c, which seemingly combine the beneficial effect of the phosphite at the 2-position with the matching (Rax)-configuration of their encumbered biaryl substituents. The results of the hydrogenation of more challenging substrates, such as Z-trisubstituted alkenes, alkenes with a neighboring polar group or demanding 1,1-di-substituted alkenes, generally confirmed this trend, and in some significant cases, the chiral hydrogenated products were isolated with ees of 65-79%. 2012 Elsevier Ltd.

Pyranoside phosphite-oxazoline ligands for the highly versatile and enantioselective Ir-catalyzed hydrogenation of minimally functionalized olefins. A combined theoretical and experimental study

A modular set of phosphite-oxazoline (P,N) ligands has been applied to the title reaction. Excellent ligands have been identified for a range of substrates, including previously challenging terminally disubstituted olefins, where we now have reached enantioselectivities of 99% for a range of substrates. The selectivity is best for minimally functionalized substrates with at least a moderate size difference between geminal groups. A DFT study has allowed identification of the preferred pathway. Computational prediction of enantioselectivities gave very good accuracy.