67928-93-2

Upstream product

• 4798-44-1 1-hexene-3-ol 
• 928-94-9 (Z)-2-hexen-1-ol 
• 142204-61-3 (-)-(R)-hex-1-en-3-yl benzoate 
• 149396-64-5 (2S,3R)-2-(bromomethyl)-3-propyloxirane 
• 14861-06-4 vinyl 2-butenoate 
• 106498-75-3 2,3-epoxyhexanol 
• 149494-24-6 [(2R,3R)-3-propoxiran-2-yl]methyl p-toluenesulfonate 
• 89321-71-1 (2S,3S)-3-propyl-2-oxiranemethanol 
• 142204-60-2 (2S,3R)-3-benzoyloxy-1,2-hexanediol 
• 3536-96-7 vinylmagnesium chloride 
• 123-72-8 butyraldehyde 
• 1826-67-1 vinyl magnesium bromide 
• 927-77-5 n-propylmagnesium bromide 
• 107-02-8 acrolein 

Downstream Products

• 139079-86-0 (3R)-hex-1-en-3-yl (R)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetate 
• 142204-61-3 (-)-(R)-hex-1-en-3-yl benzoate 
• 139164-92-4 (3R)-1-hexen-3-ol 
• 114490-68-5 4-((E)-Hex-2-enyl)-2-phenyl-4-trifluoromethyl-4H-oxazol-5-one 
• 98830-70-7 (E)-2-hexenyl phenyl sulfone 
• 18294-89-8 ethyl (E)-4-hexenoic acid 
• 54655-47-9 1-Hex-2-enyl-cyclohexan-1-ol 
• 54655-46-8 1-(1-Vinyl-butyl)-cyclohexan-1-ol 

Relevant academic research and scientific papers

Chromium-Catalyzed Production of Diols From Olefins

Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

Tailoring Interfacial Lewis Acid-Basic Pair on ZnO/4Mg1ZrOx Allows Dehydrogenative α-Methylenation of Alcohols with Methanol to Allylic Alcohols

Allylic alcohols are the essential building blocks widely used in diverse streams of organic inventions for pharmaceuticals, fragrances, agrochemicals and polymers. Currently, allylic alcohols are industrially produced from petroleum-based feedstocks via atom uneconomic processes. More sustainable synthesis route for allylic alcohols is limited. Herein, a methodology for the direct and highly selective production of allylic alcohols has been accomplished by controlled dehydrogenative α-methylenation of alcohols with methanol. This transformation is enabled by interfacial Lewis acid-basic pair on tailor-made ZnO/4Mg1ZrOx mixed oxide. High selectivity (83～92%) of allylic alcohols is the consequence of alcohols acceptorless dehydrogenation to liberation of H2 and Meerwein-Ponndorf-Verley type hydrogen transfer onto C = O bonds of unsaturated aldehydes. Furthermore, the prepared ZnO/4Mg1ZrOx mixed oxide shows good stability after 200 h time on stream test. These observations could additionally allow us to design multifunctional solid acid-basic catalysts for the transformations of renewable oxygenates into value-added chemicals.

Ruthenium(II)-Catalyzed Regio- and Stereoselective C-H Allylation of Indoles with Allyl Alcohols

A ruthenium-catalyzed C-H allylation of indoles with allyl alcohols via β-hydroxide elimination is reported. Without external oxidants and expensive additives, this reaction features mild reaction conditions, compatibility with various functional groups, and good to excellent regioselectivity and stereoselectivity.

Enantioselective addition of selenosulfonates to α,β-unsaturated ketones

An organo-catalyzed enantioselective addition of selenosulfonates to α,β-unsaturated ketones was developed for the first time. With a chiral squaramide as an efficient catalyst, the desired α-selenylated ketones were obtained in a good yields with high enantioselectivity up to 89% ee, and good results could be obtained on a gram scale. The products could also be efficiently transformed into useful building blocks with a propenylic stereocenter; the strategy presented in this study may find further applications in organic synthesis.

A Re2O7catalyzed cycloetherification of monoallylic diols

A Re2O7catalyzed cycloetherification of monoallylic diols is described. The reaction features short reaction time, mild reaction conditions and exclusive E selectivity. A wide range of monoallylic alcohols with alkyl or aryl substituents on olefin smoothly undergo ring closure to deliver corresponding oxa-heterocycles. The reaction is also operationally simple and not sensitive to air and moisture.

Rhodium-Catalyzed Asymmetric N?H Functionalization of Quinazolinones with Allenes and Allylic Carbonates: The First Enantioselective Formal Total Synthesis of (?)-Chaetominine

An unprecedented asymmetric N?H functionalization of quinazolinones with allenes and allylic carbonates was successfully achieved by rhodium catalysis with the assistance of chiral bidentate diphosphine ligands. The high efficiency and practicality of this method was demonstrated by a low catalyst loading of 1 mol % as well as excellent chemo-, regio-, and enantioselectivities with broad functional group compatibility. Furthermore, this newly developed strategy was applied as key step in the first enantioselective formal total synthesis of (?)-chaetominine.

Design and synthesis of nanoporous perylene bis-imide linked metalloporphyrin frameworks and their catalytic activity

Two nanoporous perylene bis-imide linked metalloporphyrin framework catalysts have been synthesized via condensation of 5,10,15,20-tetrakis-(4 ′ -aminophenyl) iron(III) porphyrin chloride or 5,10, 15,20-tetrakis-(4 ′ -aminophenyl) manganese(III) porphyrin chloride with perylene-3,4,9,10-tetracarboxylic dianhydride. Both the materials were crystalline in nature and were characterized by electron microscopy techniques, solid-state 1H- 13C CP/MS NMR, powder X-ray diffraction (PXRD), and magnetic susceptibility measurements. The nitrogen gas physisorption study has indicated that both materials are porous in nature and have BET surface area with 653 m2/g and 974 m2/g with uniform pore size of 2.8 nm. These materials were found to act as very good heterogeneous catalysts for selective oxidation of alkanes and alkenes with tert-butyl hydroperoxide and were not degraded even after multiple uses up to 10 cycles.

Metal catalyst-free substitution of allylic and propargylic phosphates with diarylmethyl anions

Substitution of secondary allylic phosphates with the anions derived from Ar2CH2 with BuLi or LDA proceeded regioselectively and stereoselectively without a metal catalyst, affording inversion products in good yield. Similarly, propargylic phosphates gave propargylic products selectively.

Heterogeneous Gold-Catalyzed Selective Semireduction of Alkynes using Formic Acid as Hydrogen Source

A convenient and robust protocol for the selective transfer semireduction of alkynes was developed, using bio-renewable formic acid as the hydrogen source and easily handled supported gold nanoparticles as the catalyst. The catalytic system showed several attractive features such as high activity and selectivity, recyclability, scalability and adaptability to continuous operation under mild reaction conditions, thus providing a practical alternative to current methods for alkyne semireduction.

Rhodium-Catalyzed Dynamic Kinetic Asymmetric Allylation of Phenols and 2-Hydroxypyridines

Inspired by the mechanistic studies of rhodium-catalyzed atom-economic addition of carboxylate acids to allenes, a rhodium-catalyzed dynamic kinetic asymmetric allylation of different nucleophiles with racemic allylic carbonates has been developed. High regio- and enantioselectivities can be obtained under neutral conditions and, furthermore, the chemoselectivities can be controlled by different diphosphine ligands. (R,R)-QuinoxP* leads to selective O-allylation of phenols, whereas when embedding (S,S)-DIOP as the ligand, 2-naphthol is ortho-C-allylated for the first time in high enantioselectivity. To this end, hydroxypyridines can be N-allylated by RhI/(S)-DTBM-Segphos via the same intermediate as in the previously reported atom-economic addition to allenes.