54322-96-2

Upstream product

• 1209-06-9 (+/-)-2,2-Dimethyl-5-phenyl-1,3-pentanediol 
• 104-53-0 3-phenyl-propionaldehyde 
• 13206-46-7 2-bromo-2-methylpropanal 
• 57956-40-8 methyl 3-hydroxy-2,2-dimethyl-5-phenylpentanoate 
• 6651-34-9 2-methyl-1-(trimethylsilyloxy)-1-propene 

Downstream Products

• 133271-12-2 (3R)-2,2-dimethyl-5-phenylpentane-1,3-diol 

Relevant academic research and scientific papers

9-azanoradamantane N—oxyl compound and method for producing same, and organic oxidation catalyst and method for oxidizing alcohols using 9-azanoradamantane N—oxyl compound

An organocatalyst for oxidizing alcohols in which a primary alcohol is selectively oxidized in a polyol substrate having a plurality of alcohols under environmentally-friendly conditions. The organic oxidation catalyst has an oxygen atom bonded to a nitrogen atom of an azanoradamantane skeleton and at least one alkyl group at positions 1 and 5. The oxidation catalyst has higher activity than TEMPO, which is an existing oxidation catalyst, in the selective oxidation reaction of primary alcohols, and better selectivity than AZADO and 1-Me-AZADO. This DMN-AZADO can be applied to the selective oxidation reaction of primary alcohols that contributes to shortening the synthesizing process for pharmaceuticals, pharmaceutical raw materials, agricultural chemicals, cosmetics, organic materials, and other such high value-added organic compounds.

Development of an azanoradamantane-type nitroxyl radical catalyst for class-selective oxidation of alcohols

The development of 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO; 1,5-dimethyl-Nor-AZADO, 2) as an efficient catalyst for the selective oxidation of primary alcohols in the presence of secondary alcohols is described. The compact and rigid structure of the azanoradamantane nucleus confers potent catalytic ability to DMN-AZADO (2). A variety of hindered primary alcohols such as neopentyl primary alcohols were efficiently oxidized by DMN-AZADO (2) to the corresponding aldehydes, whereas secondary alcohols remained intact. DMN-AZADO (2) also has high catalytic efficiency for one-pot oxidation from primary alcohols to the corresponding carboxylic acids in the presence of secondary alcohols and for oxidative lactonization from diols.

Germanium(II)-mediated reductive cross-aldol reaction of aldehydes: Synthesis of aldols with diastereocontrolled quaternary carbon centers

anti-Selective synthesis of aldols with quaternary carbon centers was achieved by germanium(II)-mediated reductive cross-aldol reaction of tertiary α-bromo aldehydes with both aromatic and aliphatic aldehydes. One-pot direct reduction and reductive aminat

Hydroxyl-directed intermolecular ketone-olefin couplings promoted by SmI2

SmI2-promoted intermolecular ketone-olefin couplings are facilitated and stereocontrolled by hydroxyl groups incorporated within the starting materials. For example, the SmI2-induced ketone-olefin coupling reactions of α-hydroxy ketone 5 with ethyl acrylate, acrylonitrile, ethyl crotonate, and 2(5H)-furanone proceeded with high stereocontrol to afford the syn-1,2-diol products 6-9 in good yields. Excellent diastereoselectivity was achieved in the reductive couplings of β-hydroxy aldehyde 21 and erythro-β-hydroxy ketone 24 with acrylonitrile using SmI2, to produce the anti-1,3-diols 22 and 25 in good yields. The sense of the stereoselectivity was in full accord with a chelation-control model. In the proposed model, the stereochemistry of the reaction product is explained by assuming that a cyclic ketyl radical is generated during the initial single-electron reduction by SmI2. This radical species results from the chelation of the Sm(III) cation, attached to the ketyl radical, with the hydroxyl group.