56820-01-0

Upstream product

• 2216-38-8 cis,trans-2-nonylene 
• 108957-63-7 (2S,3R)-3-chloro-2-nonanol 
• 81408-34-6 (2S,3R)-2-O-benzyl-2,3-nonanediol 
• 108957-55-7 Z-3-chloro-3-nonen-2-one 

Downstream Products

• 123878-29-5 (S)-1-nonen-3-ol 
• 79646-41-6 (R)-non-1-en-3-ol 
• 6434-78-2 2-nonene 

Relevant academic research and scientific papers

Ionic Liquid Stabilized Niobium Oxoclusters Catalyzing Oxidation of Sulfides with Exceptional Activity

We present here a new class of niobium oxoclusters that are stabilized effectively by carboxylate ionic liquids. These functionalized ILs are designated as [TBA][LA], [TBA][PA], and [TBA][HPA] in this work, in which TBA represents tetrabutylammonium and LA, PA, and HPA refer to lactate, propionate, 3-hydroxypropionate anions, respectively. The as-synthesized Nb oxoclusters have been characterized by use of elemental analysis, NMR, IR, XRD, TGA, HRTEM. It was found that [TBA][LA]-stabilized Nb oxoclusters (Nb?OC@[TBA][LA]) are uniformly dispersed with an average particle size of 2–3 nm and afforded exceptionally high catalytic activity for the selective oxidation of various thioethers. The turnover number with Nb?OC@[TBA][LA] catalyst was over 56 000 at catalyst loading as low as 0.0033 mol % (1 ppm). Meantime, the catalyst also showed the high activity for the epoxidation of olefins and allylic alcohols by using only 0.065 mol % of catalyst (50 ppm). The characterization of 93Nb NMR spectra revealed that the Nb oxoclusters underwent structural transformation in the presence of H2O2 but regenerated to their initial state at the end of the reaction. In particular, the highly dispersed Nb oxoclusters can absorb a large amount of polar organic solvents and thus were swollen greatly, which exhibited “pseudo” liquid phase behavior, and enabled the substrate molecules to be highly accessible to the catalytic center of Nb oxocluster units.

Highly selective and efficient olefin epoxidation with pure inorganic-ligand supported iron catalysts

Over the past two decades, there have been major developments in the transition iron-catalyzed selective oxidation of alkenes to epoxides; a common structure found in drug, isolated natural products, and fine chemicals. Many of these approaches have enabled highly efficient and selective epoxidation of alkenes via the design of specialized ligands, which facilitates to control the activity and selectivity of the reactions catalyzed by iron atom. Herein, we report the development of the olefin epoxidation with inorganic-ligand supported iron-catalysts using 30% H2O2 as an oxidant, and the mechanism is similar to iron-porphyrin type. With the catalyst 1, (NH4)3[FeMo6O18(OH)6], various aromatic and aliphatic alkenes were successfully transformed into the corresponding epoxides with excellent yields as well as chemo- and stereo-selectivity. This catalytic system possesses the advantages of being able to avoid the use of expensive, toxic, air/moisture sensitive and commercially unavailable organic ligands. The generality of this methodology is simple to operate and exhibits high catalytic activity as well as excellent stability, which gives it the potential to be used on an industrial scale, and maybe opens a way for the catalytic oxidation reaction via inorganic-ligand coordinated iron catalysis.

Regioselective carbonylation of trans-disubstituted epoxides to β-lactones: A viable entry into syn-aldol-type products

Two new catalysts are reported for the regioselective carbonylation of trans-disubstituted epoxides to cis-β-lactones. The two catalysts display high and opposing selectivities, which generally are difficult to achieve for this class of epoxides. The resulting β-lactones are well-defined precursors for a wide variety of aldol-type compounds. Altogether, carbonylation of disubstituted epoxides is established as a viable and economical entry into syn- and anti-aldol products.

Deracemization of anti-1,2-diols leading to trans-epoxides via oxazaborolidine-mediated enantiomer-differentiating ring-cleavage of acetal derivatives

An enantioconvergent transformation of racemic anti-1,2-diols to enantiomerically enriched (71-96% ee) trans-epoxides is realized via chiral oxazaborolidine-mediated enantiomer-differentiating ring-cleavage reaction of the acetal derivatives.

ASYMMETRIC REDUCTION OF Z-3-CHLORO-3-ALKEN-2-ONES WITH FERMENTING BAKER'S YEAST

Using fermenting baker's yeast, Z-RCH=CClCOCH3 (R=C2H5, n-C5H11, n-C8H17) was reduced initially to (S)-RCH2C*HClCOCH3 in 44-84percent ee, which was further reduced to RCH2C*HClC*HOHCH3 in >98percent ee with the syn(2R,3S)/anti(2S,3R) ratios of 2.6-18.3.