68889-70-3

Upstream product

• 3277-89-2 phenethylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 104-53-0 3-phenyl-propionaldehyde 
• 1078-58-6 diphenylzinc 
• 821784-98-9 N,N-diisopropyl O-[(S)-3-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)]prop-1-yl carbamate 
• 1896-62-4 (E)-benzalacetone 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 1083-30-3 dihydrochalcone 
• 1201898-73-8 (R)-2-(1,3-diphenylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 20780-54-5 (S)-styrene oxide 
• 6921-34-2 benzylmagnesium chloride 
• 94-41-7 benzalacetophenone 
• 100-39-0 benzyl bromide 
• 26382-04-7 diisopropyl-carbamic acid phenylmethyl ester 

Downstream Products

• 175721-86-5 (2S)-piperidine-1,2-dicarboxylic acid 1-tert-butyl 2-<(1'R)-1',3'-diphenylpropyl> diester 
• 1026639-13-3 (S)-Piperidine-2-carboxylic acid (R)-1,3-diphenyl-propyl ester 

Relevant academic research and scientific papers

Enantioselective Transfer Hydrogenation of Ketones Catalyzed by a Manganese Complex Containing an Unsymmetrical Chiral PNP′ Tridentate Ligand

Manganese complexes of the types [Mn(PNP′)(Br)(CO)2] and [Mn(PNP′)(H)(CO)2] containing a tridentate ligand with a planar chiral ferrocene and a centro chiral aliphatic unit were synthesized, characterized, and tested in the enantiose

Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki–Miyaura-Coupling and Transfer-Hydrogenation Cascade

We report a means to achieve the addition of two disparate nucleophiles to the amide carbonyl carbon in a single operational step. Our method takes advantage of non-precious-metal catalysis and allows for the facile conversion of amides to chiral alcohols via a one-pot Suzuki–Miyaura cross-coupling/transfer-hydrogenation process. This study is anticipated to promote the development of new transformations that allow for the conversion of carboxylic acid derivatives to functional groups bearing stereogenic centers via cascade processes.

Transfer Hydrogenation of Flavanones and ortho-Hydroxychalcones to 1,3-Diarylpropanols Catalyzed by CNN Pincer Ruthenium Complexes

The transfer hydrogenation of flavanones and ortho-hydroxychalcones catalyzed by ruthenium pincer complexes RuCl(CNNPh)(disphosphine) has allowed the synthesis of ortho-hydroxy 1,3-diarypropanols in 80–88 % yield, under mild reaction conditions and short reaction times (1 h) in 2-propanol. The amount of the co-catalyst NaOiPr has been found crucial for the selective reduction of flavanones to ortho-hydroxy 1,3-diarypropanols vs. flavan-4-ols. Preliminary results show that with pincer catalysts bearing (S,R)-Josiphos, flavanone is reduced to the corresponding (S)-alcohol in moderate conversion (36 %) and up to 92 % ee.

Room-Temperature Guerbet Reaction with Unprecedented Catalytic Efficiency and Enantioselectivity

We report herein an unprecedented highly efficient Guerbet-type reaction at room temperature (catalytic TON up to >6000). This β-alkylation of secondary methyl carbinols with primary alcohols has significant advantage of delivering higher-order secondary alcohols in an economical, redox-neutral fashion. In addition, the first enantioselective Guerbet reaction has also been achieved using a commercially available chiral ruthenium complex to deliver secondary alcohols with moderate yield and up to 92 % ee. In both reactions, the use of a traceless ketone promoter proved to be beneficial for the catalytic efficiency.

Asymmetric Guerbet Reaction to Access Chiral Alcohols

The first example of an asymmetric Guerbet reaction has been developed. Using commercially available, classic Noyori RuII-diamine-diphosphine catalysts, well-known in asymmetric hydrogenation, racemic secondary alcohols are shown to couple with primary alcohols in the presence of a base, affording new chiral alcohols with enantiomeric ratios of up to 99:1. Requiring no reducing agents, the protocol provides an easy, alternative route for the synthesis of chiral alcohols. Mechanistic studies reveal that the reaction proceeds via a Ru-catalyzed asymmetric hydrogen autotransfer process in concert with a base-promoted allylic alcohol isomerization.

1,3 - Diphenyl -1 - propanol and preparation method thereof

The invention relates to 1, 3-diphenyl-1-propanol and a preparation method thereof and belongs to the technical field of chemical synthesis. The preparation method comprises that benzaldehyde and acetophenone undergo a catalytic reaction in the presence of dibenzylamine trifluoroacetate and a catalyst to produce 3-hydroxy-1, 3-diphenyl-1-propanone, and the 3-hydroxy-1, 3-diphenyl-1-propanone undergoes a Huang Minglon reduction reaction to produce 1, 3-diphenyl-1-propanol, wherein the catalyst is L-proline or D-proline. The preparation method has simple processes, realizes a low cost and prepares an optically pure product satisfying the requirements. The invention also relates to 1, 3-diphenyl-1-propanol obtained by the preparation method.

Chiral Lithium Amido Aryl Zincates: Simple and Efficient Chemo- and Enantio-Selective Aryl Transfer Reagents

An enantioselective aryl transfer is promoted using chiral tricoordinated lithium amido aryl zincates that are easily accessible reagents and whose chiral appendage is simply recovered for reuse. The arylation reaction is run in good yields (60 % average on twenty substrates) and high enantiomeric excesses (95 % ee average). This occurs whatever the ortho, meta, or para substituent borne by the substrate and a complete chemoselectivity is observed with respect to the aldehyde function. Sensitive groups such as nitriles, esters, ketones, and enolisable substrates resist to the action of the ate reagent, warranting a large scope to this methodology.

Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand

The synthesis of different metal pincer complexes coordinating to the chiral PNP ligand bis(2-((2R,5R)-2,5-dimethyl-phospholanoethyl))amine is described in detail. The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral ketones. Comparing these catalysts, the non-noble metal complexes produced best selectivities not only for aromatic substrates, but also for different kinds of aliphatic ones leading to enantioselectivities up to 99% ee. Theoretical investigations elucidated the mechanism and rationalized the selectivity. (Figure presented.).

Asymmetric Transfer Hydrogenation in Thermomorphic Microemulsions Based on Ionic Liquids

A thermomorphic ionic-liquid-based microemulsion system was successfully applied for the Ru-catalyzed asymmetric transfer hydrogenation of ketones. On the basis of the temperature-dependent multiphase behavior of the targeted microemulsion, simple product separation as well as catalyst recycling could be realized. The use of water-soluble ligands improved the immobilization of the catalyst in the microemulsion phase and significantly decreased the catalyst leaching into the organic layer upon extraction of the product. Eventually, the optimized microemulsion system could be applied to a wide range of aromatic ketones that were reduced with good isolated yields (up to 98%) and enantioselectivities (up to 97%), while aliphatic ketones were less successful.

CHIRAL METAL COMPLEX COMPOUNDS

The invention comprises novel chiral metal complex compounds of the formula (I) wherein M, PR2, R3 and R4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.