473828-52-3

Upstream product

• 100-52-7 benzaldehyde 
• 17933-29-8 7-methylenebicyclo[3.3.1]nonan-3-one 

Downstream Products

• 1146974-75-5 (R)-((1R,2S,5S)-7-methylene-3-oxobicyclo[3.3.1]nonan-2-yl)(phenyl)methyl-4-bromobenzoate 
• 1146974-76-6 (1R,2S,5S)-2-benzyl-7-methylbicyclo[3.3.1]non-7-en-3-one 
• 1146974-39-1 (1R,2S,5R)-2-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-one 
• 1146974-80-2 N-((1S,3R,4S,5R)-4-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine 
• 1146974-46-0 N-((1R,2S,3R,5R)-2-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-yl)hydroxylamine 
• 1146974-78-8 (3E)-(1R,2S,5S)-2-benzyl-7-methylbicyclo[3.3.1]non-7-en-3-one oxime 
• 1146974-43-7 (3E)-(1R,2S,5R)-2-benzyl-7-methylbicyclo[3.3.1]non-6-en-3-one oxime 
• 473828-55-6 (1R,2R,5S)-7-Methylene-2-((S)-1-phenyl-ethyl)-bicyclo[3.3.1]nonan-3-one 
• 473828-53-4 (1R,5S)-2-((E)-benzylidene)-7-methylenebicyclo[3.3.1]nonan-3-one 

Relevant academic research and scientific papers

Highly enantioselective organocatalytic oxidative kinetic resolution of secondary alcohols using chiral alkoxyamines as precatalysts: Catalyst structure, active species, and substrate scope

The development and characterization of enantioselective organocatalytic oxidative kinetic resolution (OKR) of racemic secondary alcohols using chiral alkoxyamines as precatalysts are described. A number of chiral alkoxyamines have been synthesized, and their structure-enantioselectivity correlation study in OKR has led us to identify a promising precatalyst, namely, 7-benzyl-3-n-butyl-4-oxa-5-azahomoadamantane, which affords various chiral aliphatic secondary alcohols (ee up to >99%, krel up to 296). In a mechanistic study, chlorine-containing oxoammonium species were identified as the active species generated in situ from the alkoxyamine precatalyst, and it was revealed that the chlorine atom is crucial for high reactivity and enantioselectivity. The present OKR is the first successful example applicable to various unactivated aliphatic secondary alcohols, including heterocyclic alcohols with high enantioselectivity, the synthetic application of which is demonstrated by the synthesis of a bioactive compound.

Highly enantioselective organocatalytic oxidative kinetic resolution of secondary alcohols using chirally Modified AZADOs

A highly enantioselective organocatalytic oxidative kinetic resolution (OKR) of racemic secondary alcohols has been accomplished using asymmetric organocatalysis. A panel of chirally modified 2-azaadamantane N-oxyls (AZADOs) exhibit superior catalytic act

Chiral modification of adamantane

Three optically active adamantane derivatives have been constructed starting from meso 7-methylidenebicyclo[3.3.1]nonan-3-one by employing two chirality induction processes, asymmetric aldolization and Sharpless asymmetric epoxidation.