71434-60-1

Upstream product

• 693-25-4 n-pentylmagnesium bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 71-36-3 butan-1-ol 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1240790-33-3 1-(4-methoxyphenyl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexane 
• 110-53-2 1-Bromopentane 
• 6397-82-6 4'-methoxyhexanophenone 
• 108-05-4 vinyl acetate 
• 129145-41-1 1-(4-methoxylphenyl)-1-hexanol 
• 1570511-02-2 (R)-2-(1-(4-methoxyphenyl)hexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 58133-26-9 1,1-dibromohexane 
• 66-25-1 hexanal 
• 544-12-7 3-hexen-1-ol 

Downstream Products

• 107441-84-9 (E)-1-(hex-1-enyl)-4-methoxybenzene 
• 6397-82-6 4'-methoxyhexanophenone 
• 71434-60-1 (R)-1-(4-methoxylphenyl)-1-hexanol 
• 129145-43-3 C₁₅H₂₂O₃ 
• 71434-02-1 1-(p-Methoxyphenyl)-1-hexylchlorid 

Relevant academic research and scientific papers

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.

Multicatalytic approach to one-pot stereoselective synthesis of secondary benzylic alcohols

One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).

Catalytic asymmetric arylation of aliphatic aldehydes using a B/Zn exchange reaction

Herein we describe the arylation of aliphatic aldehydes using the boron/zinc exchange reaction for the generation of transferable aryl groups, in the presence of chiral amino alcohol ligands. For the first time, a systematic investigation of this reaction

Tandem α-Alkylation/Asymmetric Transfer Hydrogenation of Acetophenones with Primary Alcohols

Tandem α-alkylation/asymmetric transfer hydrogenation of acetophenones with primary alcohols, mediated by a single ruthenium catalyst, is described. Under optimized reaction conditions and with use of [Ru(p-cymene)Cl2]2 in combination with an amino acid hydroxyamide ligand, the chiral secondary alcohol products were isolated in moderate yields and in moderate to good enantiomeric excess (up to 89 % ee). One catalyst - one pot - two reactions. Acetophenones are initially alkylated with primary alcohols by the borrowing hydrogen methodology. The alkylation products are directly converted to enantiomerically enriched secondary alcohols.

A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates

Catalytic enantiotopic-group-selective cross-couplings of achiral geminal bis(pinacolboronates) provide a route for the construction of nonracemic chiral organoboronates. In the presence of a chiral monodentate taddol-derived phosphoramidite ligand, these reactions occur with high levels of asymmetric induction. Mechanistic experiments with chiral 10B-enriched geminal bis(boronates) suggest that the reaction occurs by a stereochemistry-determining transmetalation that occurs with inversion of configuration at carbon.

Redesign of enzyme for improving catalytic activity and enantioselectivity toward poor substrates: Manipulation of the transition state

Secondary alcohols having bulky substituents on both sides of the hydroxy group are inherently poor substrates for most lipases. In view of this weakness, we redesigned a Burkholderia cepacia lipase to create a variant with improved enzymatic characteristics. The I287F/I290A double mutant showed a high conversion and a high E value (>200) for a poor substrate for which the wild-type enzyme showed a low conversion and a low E value (5). This enhancement of catalytic activity and enantioselectivity of the variant resulted from the cooperative action of two mutations: Phe287 contributed to both enhancement of the (R)-enantiomer reactivity and suppression of the (S)-enantiomer reactivity, while Ala290 created a space to facilitate the acylation of the (R)-enantiomer. The kinetic constants indicated that the mutations effectively altered the transition state. Substrate mapping analysis strongly suggested that the CH/π interaction partly enhanced the (R)-enantiomer reactivity, the estimated energy of the CH/π interaction being -0.4 kcal mol-1. The substrate scope of the I287F/I290A double mutant was broad. This biocatalyst was useful for the dynamic kinetic resolution of a variety of bulky secondary alcohols for which the wild-type enzyme shows little or no activity. The Royal Society of Chemistry 2012.

Chemoselective and regiospecific suzuki coupling on a multisubstituted sp3-Carbon in 1,1-diborylalkanes at room temperature

The palladium-catalyzed Suzuki-Miyaura cross-coupling on a multisubstituted sp3-carbon in 1,1-diborylalkanes was achieved at room temperature. The generation of a monoborate intermediate by virtue of the adjacent B atom could result in the chemoselective coupling reaction under ambient conditions.

A catalytic deracemisation of alcohols

Racemic alcohols have been converted into enantiomerically enriched alcohols with up to 99% ee in a one-pot oxidation/reduction procedure. The Royal Society of Chemistry.

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.

Direct β-alkylation of secondary alcohols with primary alcohols catalyzed by a Cp*Ir complex

(Chemical Equation Presented) A new catalytic system for β-alkylation of secondary alcohols has been developed. In the presence of [Cp*IrCl 2]2 (Cp* = pentamethylcyclopentadienyl) catalyst and base, the reactions of various secondary alcohols with primary alcohols give β-alkylated higher alcohols in good to excellent yields without any hydrogen acceptor or hydrogen donor. This reaction proceeds via successive hydrogen-transfer reactions and aldol condensation.