57243-11-5

Upstream product

• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 14263-32-2 lithium tetrabutylaluminate 
• 693-25-4 n-pentylmagnesium bromide 
• 122-78-1 phenylacetaldehyde 
• 94417-52-4 (Bis-methylselanyl-methyl)-benzene 
• 66-25-1 hexanal 
• 78-84-2 isobutyraldehyde 
• 55791-06-5 benzyl mesylate 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 
• 71-41-0 pentan-1-ol 
• 5281-18-5 benzaldehyde, hydrazone 
• 928-94-9 (Z)-2-hexen-1-ol 
• 928-95-0 (E)-2-Hexen-1-ol 

Downstream Products

• 65899-16-3 5-phenyl-6-undecanone 
• 6683-94-9 1-Phenyl-2-heptanone 

Relevant academic research and scientific papers

A General Regioselective Synthesis of Alcohols by Cobalt-Catalyzed Hydrogenation of Epoxides

A straightforward methodology for the synthesis of anti-Markovnikov-type alcohols is presented. By using a specific cobalt triphos complex in the presence of Zn(OTf)2 as an additive, the hydrogenation of epoxides proceeds with high yields and selectivities. The described protocol shows a broad substrate scope, including multi-substituted internal and terminal epoxides, as well as a good functional-group tolerance. Various natural-product derivatives, including steroids, terpenoids, and sesquiterpenoids, gave access to the corresponding alcohols in moderate-to-excellent yields.

Synergistic Relay Reactions To Achieve Redox-Neutral α-Alkylations of Olefinic Alcohols with Ruthenium(II) Catalysis

Herein, we report a ruthenium-catalyzed redox-neutral α-alkylation of unsaturated alcohols based on a synergistic relay process involving olefin isomerization (chain walking) and umpolung hydrazone addition, which takes advantage of the interaction between the two rather inefficient individual reaction steps to enable an efficient overall process. This transformation shows the compatibility of hydrazone-type “carbanions” and active protons in a one-pot reaction, and at the same time achieves the first Grignard-type nucleophilic addition using olefinic alcohols as latent carbonyl groups, providing a higher yield of the corresponding secondary alcohol than the classical hydrazone addition to aldehydes does. A broad scope of unsaturated alcohols and hydrazones, including some complex structures, can be successfully employed in this reaction, which shows the versatility of this approach and its suitability as an alternative, efficient means for the generation of secondary and tertiary alcohols.

Direct Conversion of Alcohols into Alkenes by Dehydrogenative Coupling with Hydrazine/Hydrazone Catalyzed by Manganese

We have developed unprecedented methods for the direct transformation of primary alcohols to alkenes in the presence of hydrazine, and for the synthesis of mixed alkenes by the reaction of alcohols with hydrazones. The reactions are catalyzed by a manganese pincer complex and proceed in absence of added base or hydrogen acceptors, liberating dihydrogen, dinitrogen, and water as the only byproducts. The proposed mechanism, based on preparation of proposed intermediates and control experiments, suggests that the transformation occurs through metal–ligand cooperative N?H activation of a hydrazone intermediate.

Pd-catalyzed cleavage of benzylic nitro bonds: New opportunities for asymmetric synthesis

Without a trace: Benzylic nitroalkanes are reduced to the corresponding parent alkanes in good yields by using a simple procedure involving heterolytic C-N bond cleavage (see scheme). Traceless removal of the nitro group leaves behind a stereogenic center that may otherwise be difficult to install. This reaction significantly expands the scope of building blocks that can be accessed. (Chemical Equation Presented)

Direct preparation of benzylic manganese reagents from benzyl halides, sulfonates, and phosphates and their reactions: Applications in organic synthesis

The use of highly active manganese (Mn)*, prepared by the Rieke method, was investigated for the direct preparation of benzylic manganese reagents. The oxidative addition of the highly active manganese to benzylic halides was easily completed under mild conditions. Moreover, benzylic manganese sulfonates and phosphates were prepared by direct oxidative addition of Mn* to the carbon-oxygen bonds of benzylic sulfonates and phosphates. The resulting benzylic manganese reagents were found to undergo cross-coupling reactions with a variety of electrophiles. Most of these reactions were carried out in the absence of any transition metal catalyst under mild conditions. In addition, the use of highly active manganese was also studied for preparation of homo-coupled products of functionalized benzyl halides without transition metal catalysts. These useful approaches provided not only a facile synthetic route to the preparation of resoricinolic lipids but a facile synthesis of functionalized 4-benzylpyridines by regioselective and chemo selective γ-addition of benzylic group to N-alkoxycarbonylpyridinum salts.

Benzylic Manganese Halides, Sulfonates, and Phosphates: Preparation, Coupling Reactions, and Applications in Organic Synthesis

The use of highly active manganese, prepared by the Rieke method, for the direct preparation of benzylic manganese reagents was investigated. The oxidative addition of the highly active manganese (Mn*) to benzylic halides was easily completed under mild conditions. More importantly, benzylic manganese sulfonates and phosphates were prepared by direct oxidative addition of Mn* to the carbon-oxygen bonds of benzylic sulfonates and phosphates. The resulting benzylic manganese reagents were found to undergo cross-coupling reactions with a variety of electrophiles. The majority of these reactions were carried out in the absence of any transition metal catalyst under mild conditions. This approach also provided a facile synthetic route to the preparation of resorcinolic lipids.

A new synthetic protocol for the direct preparation of organomanganese reagents; organomanganese tosylates and mesylates

A new synthetic route to organomanganese sulfonate reagents has been developed. These useful reagents can be readily prepared via direct oxidative addition of highly reactive manganese to carbon-oxygen bonds of the corresponding tosylates and mesylates under mild conditions.

C/Se bond cleavage of functionalized selenides by lithium arenides: Application to the geminal di-allylation of the carbonyl group of aldehydes and ketones

Selenoacetals as well as mixed (O,Se) acetals react with lithium arenides and produce, besides lithium selenolates, α-selenoalkyllithiums or α-alkoxyalkyllithiums respectively. We took advantage of these reactions as well as of the ones involving the synthesis of alkyllithiums from selenides to propose an original method for geminal di-allylation of the carbonyl group of aldehydes and ketones.

Substituted 2-Pyrones, 2-Pyridones, and Other Congeners of Elasnin as Potential Agents for the Treatment of Chronic Obstructive Lung Diseases

Several congeners of elasnin (I) have been synthesized and shown to inhibit human leukocyte elastase (HLE).The C-3 alkyl substituted 2-pyrones 11 and 12 were found to be most inhibitors of the enzyme.These compounds are highly specific in their inhibitory