113725-16-9

Upstream product

• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 447-53-0 1,2-Dihydronaphthalene 
• 530-91-6 1,2,3,4-tetrahydronaphthalen-2 ol 
• 766-77-8 Dimethylphenylsilane 
• 108-05-4 vinyl acetate 
• 51268-88-3 (1R,2S)-1,2-dihydronaphthalene-1,2-diol 
• 939760-68-6 4,6-Difluoro-1a,2,3,7b-tetrahydro-1-oxa-cyclopropa[a]naphthalene 
• 124867-52-3 C₁₆H₂₂O₅ 
• 7576-04-7 (R)-(Indanylcarbinyl-1)-p-toluolsulfonat 
• 71601-10-0 (RS)-1,2,3,4-tetrahydro-2-naphthol acetate 
• 1130490-92-4 4,4,5,5-tetramethyl-2-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane 
• 115276-25-0 2R-2-hydroxyl (2H)-naphthalenone (2S,3S)-1,4-dimethoxy-2,3-butylene acetal 
• 173996-16-2 5,7-Difluoro-1,2,3,4-tetrahydro-naphthalen-1-ol 
• 939760-86-8 6,8-Difluoro-1,2-dihydro-naphthalene 

Downstream Products

• 1374428-96-2 (S)-((S)-1,2,3,4-tetrahydronaphthalen-2-yl) 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 
• 2217-42-7 (2R)-2-amino-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

Synthesis of (R)-BINOL-Derived (Cyclopentadienone)iron Complexes and Their Application in the Catalytic Asymmetric Hydrogenation of Ketones

A family of chiral (cyclopentadienone)iron complexes, featuring an (R)-BINOL-derived backbone, and their application in the asymmetric hydrogenation of ketones are described. The complexes differ from each other in the substituents at the 3,3′-positions of the binaphthyl residue (H, OH, OR, OCOR, OSO2R) or at the 2,5-positions of the cyclopentadienone ring [trimethylsilyl (TMS) or Ph]. Remarkably, eight precatalysts with different 3,3′-binaphthyl substitution [(R)-1c-1j] were synthesized from a common parent complex [(R)-1b] through direct functional group interconversion reactions of the complexes. The 3,3′-(bis)methoxy-substituted precatalyst (R)-1b gave the best catalytic performance, and its application scope was assessed in the hydrogenation of several ketones. The observed ee values (up to 77%) are much higher than those previously reported for other chiral (cyclopentadienone)iron complexes.

Asymmetric reduction of methoxy substituted β-tetralones using transfer hydrogenation

Asymmetric reductions of methoxy substituted 2-tetralones were studied. The asymmetric transfer hydrogenation reaction developed by Noyori using chiral η6-arene-ruthenium complexes (arene = p-cymene or benzene) was found to efficiently reduce various methoxy substituted 2-tetralones with >80% ee. Their enantiomeric excesses were found to depend on the position of the methoxy group and the types of the arene complexes. The conditions were identified for the asymmetric reduction of 8-methoxy-2-tetralone to the corresponding 2-tetralol in 98% ee, which was notably higher in enantioselectivity than the other methoxy substituted 2-tetralones.

ASYMMETRIC REDUCTION OF PROCHIRAL CYCLIC KETONES WITH LITHIUM ALUMINIUM HYDRIDE PARTIALLY DECOMPOSED BY (1R,2S)-(-)-N-METHYLEPHEDRINE AND 2-ALKYLAMINOPYRIDINE

The title chiral hydride was found to reduce prochiral cyclic ketones, affording the corresponding optically active cyclic alcohols in high optical (max. 98percentee) yields.

Xerogel-encapsulated W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus performs asymmetric reduction of hydrophobic ketones in organic solvents

To gel well: The asymmetric reduction of hydrophobic ketones by xerogel-immobilized W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus (TeSADH) in organic solvents affords their S-configured alcohols in yields comparable with those achieved by using the free enzyme, and, in some cases, with higher enantioselectivities. R = phenyl-ring-containing substituent. (Figure Presented).

Preparation of chiral ligands connected with quaternary ammonium group for recyclable catalytic asymmetric transfer hydrogenation in ionic liquid

Reuse of chiral ruthenium catalyst in catalytic asymmetric transfer hydrogenation (CATH) has attracted attention from economic and environmental viewpoints, and reactions using ionic liquids (ILs) as solvent are recognized as one of the most useful methods for reuse of the catalyst. We synthesized (1 S,2 S )- N-( p - toluenesulfonyl)-1,2-diphenylethylenediamine (TsDPEN) derivatives with various ionic moieties, and investigated the effect of their structure with respect to catalytic ability and recyclability in CATH with ILs. Ligand 3a having an imidazolium group showed the best results, and significant differences were observed depending on the structure of the ionic moiety or the length of the alkyl chain connecting the ligand site and the ionic moiety. Among various prochiral ketones used as substrates at various cycles, 3a showed a relatively good result.

Asymmetric hydrosilylation of alkenes with alkoxyhydrosilanes catalyzed by chiral bis(oxazolinyl)phenyl-rhodium complex

Asymmetric addition of alkoxyhydrosilanes to styrene derivatives was examined with chiral bis(oxazolinyl)phenyl-rhodium complex to give moderate ratios (up to 77:23) of α- and β-adducts and high enantioselectivity (up to 95% for the α-adduct).

Access to both enantiomers of substituted 2-tetralol analogs by a highly enantioselective reductase

Both (S) and (R) forms of enantiomerically pure 2-tetralols, and their substituted analogs, are fundamental pharmaceutical intermediates. Here, we utilized the wild type and an engineered form of a highly enantioselective acetophenone reductase from Geotrichum candidum NBRC 4597 (GcAPRD) to produce (S)- and (R)-2-tetralols, and their substituted analogs. All mutations targeted residue Trp288, which has been shown to restrict substrate binding, but not play a direct role in catalysis. The wild type produced (S)-alcohols with excellent enantioselectivity, while the engineered forms produced either (S)- or (R)- alcohols, depending on the substituent on the aromatic ring of the substrate, indicating that enantioselectivity can be rationally controlled. As a result, we were able to produce 6-hydroxy-2-tetralol, a potential antifungal drug intermediate, with 98% ee (S) and 81% ee (R) by wild type and Trp288Ser GcAPRD, respectively. To our knowledge, this is the first report of generating chiral 6-hydroxy-2-tetralol by rational enzyme design.

Highly efficient asymmetric transfer hydrogenation of ketones catalyzed by chiral 'roofed' cis-diamine-Ru(II) complex

A new type of chiral Ru(II) complex, prepared from a conformationally rigid, sterically bulky 'roofed' cis-diamine and [RuCl2(benzene)] 2, functions as an efficient catalyst for the asymmetric transfer hydrogenation of a wide variety of aryl ketones, including sterically bulky ketones, when the reaction is conducted in the presence of 5HCO 2H?2NEt3.

Chemical and chemotaxonomical studies of ferns. LXXXIV. A novel 2-tetralol-type xyloside from Asplenium wilfordii

A novel 2-tetralol-type xyloside, named asplenoside, was isolated from the fronds of Asplenium wilfordii. The structure was determined as (6R)-5,6,7,8-tetrahydro-6-β-D-xylopyranosyloxy-2-naphthalenecarboxyli c acid by chemical and spectral means. Application of the glycosylation shift rule in 13C-NMR spectroscopy to the determination of the absolute configuration is described.

Organic-inorganic nanocrystal reductase to promote green asymmetric synthesis

An acetophenone reductase from Geotrichum candidum (GcAPRD) was immobilized by the organic-inorganic nanocrystal method. The GcAPRD nanocrystal presented improved stability and recyclability compared with those of the free GcAPRD. Moreover, the GcAPRD nanocrystal reduced broad kinds of ketones with excellent enantioselectivities to produce beneficial chiral alcohols such as (S)-1-(3′,4′-dichlorophenyl)ethanol with >99% yield and >99% ee. The robust and versatile properties of the GcAPRD nanocrystal demonstrated an approach to promote green asymmetric synthesis and sustainable chemistry. This journal is