106623-83-0

Upstream product

• 110-53-2 1-Bromopentane 
• 100-52-7 benzaldehyde 
• 14402-93-8 dipentylzinc 
• 693-25-4 n-pentylmagnesium bromide 
• 6111-82-6 (E)-1-phenyl-1-hexene 
• 942-92-7 caprophenone 
• 4471-05-0 1-phenylhexan-1-ol 
• 109-72-8 n-butyllithium 
• 20780-54-5 (S)-styrene oxide 
• 108-05-4 vinyl acetate 
• 66-25-1 hexanal 
• 98-80-6 phenylboronic acid 
• 1129-65-3 (hex-1-yn-1-yl)benzene 
• 544-12-7 3-hexen-1-ol 

Relevant academic research and scientific papers

Enantioselective 1,2-addition of Grignard reagents to aldehydes using chiral diamines

Enantioselective 1,2-addition of Grignard reagents to aldehydes using chiral diamine 1, 2 was examined. High ee (up to 75%) of carbinol was achieved by the reaction of arylmagnesium bromide and benzaldehyde with chiral diamine. Utilizing 2,4,6-trimethylph

One-way biohydrogen transfer for oxidation of sec-alcohols

(Chemical Equation Presented) Quasi-irreversible oxidation of sec-alcohols was achieved via biocatalytic hydrogen transfer reactions using alcohol dehydrogenases employing selected ketones as hydrogen acceptors, which can only be reduced but not oxidized. Thus, only 1 equiv of oxidant was required instead of a large excess. For the oxidation of both isomers of methylcarbinols a single nonstereoselective short-chain dehydrogenase/reductase from Sphingobium yanoikuyae was identified and overexpressed in E. coli.

Stereocomplementary asymmetric reduction of bulky-bulky ketones by biocatalytic hydrogen transfer

Biocatalysts suitable for the reduction of ketones bearing two sterically demanding substituents (bulky-bulky ketones) at elevated substrate concentration (10 gL-1) were identified. The biocatalysts can be employed in a substrate-coupled approa

Enhancement of enantioselectivity by alcohol additives in asymmetric hydrogenation with bis(oxazolinyl)phenyl ruthenium catalysts

Bis(oxazolinyl)phenyl ruthenium(ii) complexes were found to catalyze asymmetric hydrogenation of ketones, in which chiral bulky alcohol additives showed significant enhancement of enantioselectivity even in protic solvents. The Royal Society of Chemistry 2012.

Is it possible to estimate the enantioselectivity of a chiral catalyst from its racemic mixture?

The evaluation of a racemic catalyst was investigated in the case of oxazaborolidine (OAB)-catalyzed borane reduction of 1,5-diphenyl-1,5-pentanedione, giving the corresponding diol. On the basis of the diastereoselectivity of the diols, it is possible to estimate the enantioselectivity (ee) of the first step, which correlates well with the ee in the reaction of the structurally similar phenyl n-pentyl ketone with enantiopure OAB catalyst. The measure of diastereoselectivity could be a tool for screening racemic catalysts without the need for resolving the individual enantiomers, if in the second step of the process there is no substrate control and no catalyst scrambling. Copyright

Stereoselective bioreduction of bulky-bulky ketones by a novel ADH from Ralstonia sp.

(Figure Presented) Ketones with two bulky substituents, named bulky-bulky ketones, as well as less sterically demanding ketones were successfully reduced to the corresponding optically highly enriched alcohols using a novel identified recombinant short-chain alcohol dehydrogenase RasADH from Ralstonia sp. DSM 6428 overexpressed in E. coli.

Neopentyl and neophyl groups: New nontransferable groups for organocopper and organozinc chemistry

Neopentyl and Neophyl groups have been found to be excellent nontransferable groups for organozinc and organocopper chemistry. We have shown that mixed diorganozincs of the type FG-R-Zn(CH2CMe2R) can be used advantageously for the enantioselective addition to aldehydes. These mixed copper or zinc reagents are also found to be very efficient in the Michael addition to various activated alkenes.

NOVEL USE OF ARYLOXYALUMINIUM DICHLORIDE IN THE CHIRAL DIAMINE MEDIATED ASYMMETRIC ADDITION REACTION OF GRIGNARD REAGENTS TO BENZALDEHYDE

Utilizing 2,4,6-trimethylphenoxyaluminium dichloride (3) as a coordinating agent to benzaldehyde, asymmetric addition reaction of Grignard reagent-chiral diamine (1 or 2) complexes has been shown to afford the corresponding carbinols in good enantioselect

Ir- and Ru-catalyzed sequential reactions: Asymmetric α-alkylative reduction of ketones with alcohols

(Chemical Equation Presented) The compatibility between [{IrCl(cod)} 2] and ruthenium complex 1 to achieve asymmetric α-alkylative reduction of prochiral ketones with primary alcohols is an essential factor in obtaining optically active alcohols with elongation of the carbon skeleton in good yields with a high enantioselectivity.

A relay catalysis strategy for enantioselective nickel-catalyzed migratory hydroarylation forming chiral α-aryl alkylboronates

Ligand-controlled reactivity plays an important role in transition-metal catalysis, enabling a vast number of efficient transformations to be discovered and developed. However, a single ligand is generally used to promote all steps of the catalytic cycle (e.g., oxidative addition, reductive elimination), a requirement that makes ligand design challenging and limits its generality, especially in relay asymmetric transformations. We hypothesized that multiple ligands with a metal center might be used to sequentially promote multiple catalytic steps, thereby combining complementary catalytic reactivities through a simple combination of simple ligands. With this relay catalysis strategy (L/L?), we report here the first highly regio- and enantioselective remote hydroarylation process. By synergistic combination of a known chain-walking ligand and a simple asymmetric cross-coupling ligand with the nickel catalyst, enantioenriched α-aryl alkylboronates could be rapidly obtained as versatile synthetic intermediates through this formal asymmetric remote C(sp3)-H arylation process.