16958-19-3

Upstream product

• 623-36-9 (E)-2-methylpent-2-enal 
• 1617-40-9 ethyl (E)-2-methyl-2-pentenoate 
• 16957-70-3 2-methylpent-2-enoic acid 
• 36219-40-6 1-bromo-2-hydroxy-2-methyl-3-butene 
• 917-54-4 methyllithium 
• 5673-98-3 2-methylpent-4-en-1-ol 
• 30018-16-7 (1-ethoxycarbonylethyl)triphenylphosphonium bromide 
• 123-38-6 propionaldehyde 
• 1567-14-2 methyl (2E)-2-methyl-2-pentenoate 

Downstream Products

• 32475-72-2 3,5-dimethyl-tetrahydropyran-2-one 
• 3290-57-1 3,5-dimethyl-tetrahydropyran-2-one 
• 123411-58-5 (2R,3R)-2-Methyl-1-phenylsulfanyl-pentane-2,3-diol 
• 122358-36-5 Toluene-4-sulfonic acid (4S,5S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-heptyl ester 
• 72522-40-8 (4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone 
• 72598-35-7 (-)-serricornin 
• 72522-40-8 (4RS,6SR,7SR)-Serricornin 
• 42328-43-8 (2R,3R)/(2S,3S)-2,3-dimethylpentane 1,2-epoxide 
• 1640021-31-3 ((3S,4S,8S,E)_9-(benzyloxy)-4,8-dimethylnon-5-en-3-yloxy)(tert-butyl)dimethylsilane 
• 335673-29-5 tert-butyl (2S)-2-{(1S,2S)-2-methoxy-1-[(4-methoxyphenyl)amino]-2-methylpentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 471257-47-3 (1E,2S)-2-methoxy-2-methylpentanal S-tritylthioxime 
• 1026253-35-9 [(S)-2-Methoxy-2-methyl-pent-(E)-ylidene]-(4-methoxy-phenyl)-amine 
• 335637-15-5 ((((2S)-2-methoxy-2-methylpentyl)oxy)methyl)benzene 
• 335637-14-4 (2S)-1-(benzyloxy)-2-methyl-2-pentanol 

Relevant academic research and scientific papers

Copper-Catalyzed Stereospecific Hydroboration of Internal Allylic Alcohols

An effective Cu-catalyzed stereospecific hydroboration of aliphatic and aromatic 1,1,2-trisubstituted internal allylic alcohols has been reported. This reaction proceeds via a silyl ether transient protection of allylic alcohols and subsequent stereospecific hydroboration. Followed by an oxidative workup, an array of acyclic, cyclic, and heterocyclic 1,3-diols was synthesized in good to excellent yields with good functional group tolerance and excellent diastereomeric ratios (> 20:1).

Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes

Intramolecular chirality transfer [2 + 2] cycloaddition of enantiomerically enriched allenoates and alkenes is presented. The use of a chiral catalyst was found to be critical to achieve high levels of diastereoselectivity compared to use of an achiral catalyst. The method developed leads to highly substituted cyclobutanes that would be difficult to prepare by alternative methods.

Selective Pinacol-Coupling Reaction using a Continuous Flow System

The first continuous flow pinacol coupling reaction of carbonyl compounds was successfully achieved within only 2 min during a single pass through a cartridge filled with zinc(0). The optimized method allowed the efficient production of gram-scale value-added compounds with high productivity. The developed methodology is efficient for aromatic or α,β-unsaturated aldehydes but gives moderate results for more stable acetophenone derivatives. Moreover, the flow method displayed better results in terms of yield and selectivity in comparison to the corresponding batch methodology.

Electronic interactions between a stable electride and a nano-alloy control the chemoselective reduction reaction

Controlling the electronic structure of heterogeneous metal catalysts is considered an efficient method to optimize catalytic activity. Here, we introduce a new electronic effect induced by the synergy of a stable electride and bimetallic nanoparticles for a chemoselective reduction reaction. The electride [Ca24Al28O64]4+·(e-)4, with extremely low work function, promotes the superior activity and selectivity of a Ru-Fe nano-alloy for the conversion of α,β-unsaturated aldehydes to unsaturated alcohols in a solvent-free system. The catalyst is easily separable from the product solution and reusable without notable deactivation. Mechanistic studies demonstrate that electron injection from the electride to the Ru-Fe bimetallic nanoparticles promotes H2 dissociation on the highly charged active metal and preferential adsorption of CO bonds over CCs bond of the unsaturated aldehydes, to obtain the thermodynamically unfavorable but industrially important product.

Borinic Acid Catalyzed, Regioselective Chloroacylations and Chlorosulfonylations of 2,3-Epoxy Alcohols

In the presence of a borinic acid derived catalyst, 2,3-epoxy alcohols undergo couplings with acyl and sulfonyl chlorides. This transformation directly generates O-acylated or O-sulfonylated chlorohydrin diols, with significant levels of regioselectivity for both the ring-opening and O-functionalization steps.

First pinacol coupling in emulsified water: Key role of surfactant and impact of alternative activation technologies

For the first time, the influence of surfactants on the radical pinacol coupling reaction is investigated. The rate and selectivity of this reductive C-C coupling are compared under three different activation technologies: thermal activation, microwave irradiation, and sonication. The use of IgepalCO520, a neutral surfactant, led to the successful conversion of aromatic or α,β-unsaturated aliphatic carbonyl compounds in moderate to excellent yield (55-90 %). An insight on the potential mechanism involved in the reaction is also proposed, based on microscopic observations and particle size measurement.

An alternative mechanism for the cobalt-catalyzed isomerization of terminal alkenes to (Z)-2-alkenes

The cobalt-catalyzed selective isomerization of terminal alkenes to the thermodynamically less-stable (Z)-2-alkenes at ambient temperatures takes place by a new mechanism involving the transfer of a hydrogen atom from a Ph2PH ligand to the starting material and the formation of a phosphenium complex, which recycles the Ph2PH complex through a 1,2-H shift.

Asymmetric synthesis of C11-C23 fragment of Pladienolide B

Synthesis of C11-C23 fragment of an antitumor natural product, Pladienolide B, in gram-scale, is described. The key steps involved in this synthesis are Julia-Kocienski olefination, opening of epoxide with TBSOTf to form the corresponding - OTBS protected

3,4-Dihydroxypyrrolidines via modified tandem aza-payne/hydroamination pathway

The outcome of a tandem aza-Payne/hydroamination reaction is modified via the use of a latent nucleophile. The latter initially serves as an electrophile to intercept the aziridine alkoxide and afterward turns into a nucleophile thereby performing the aziridine ring opening, out competing the intramolecular aza-Payne pathway. Subsequent hydroamination in the same pot provides N-Ts enamide carbonates, which can be easily converted into biologically significant 3,4-dihydroxylactams.

METHOD FOR PRODUCING ALCOHOL COMPOUND

Disclosed is a practical method for efficiently producing an alcohol compound by hydrogenating an aldehyde by using a homogeneous copper catalyst which is an easily-available low-cost metal species. Specifically disclosed is a method for producing an alcohol compound, which is characterized in that a hydrogenation reaction of an aldehyde compound is performed in the presence of a homogeneous copper catalyst and a diphosphine compound.