221099-70-3

Upstream product

• 108-86-1 bromobenzene 
• 125637-45-8 (1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid methylester 
• 464-78-8 (1S)-(+)-ketopinic acid 
• 591-51-5 phenyllithium 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 1420814-23-8 2-((R)-2,2-dimethyl-3-(diphenylmethylene)cyclopentyl)acetic acid 
• 249739-62-6 Oxo-phenyl-acetic acid (1S,2R,4R)-1-(methoxy-diphenyl-methyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 249739-65-9 2-Oxo-butyric acid (1S,2R,4R)-1-(hydroxy-diphenyl-methyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 249739-64-8 2-Oxo-propionic acid (1S,2R,4R)-1-(hydroxy-diphenyl-methyl)-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 249739-60-4 exo-10,10-diphenyl-10-methoxymethyl-7,7-dimethylbicyclo-[2.2.1]heptane-2-ol 

Relevant academic research and scientific papers

Modular iminopyridine ligands. Application to the enantioselective copper(II)-catalyzed Henry reaction

Chiral iminopyridines prepared in a modular fashion from monoterpenic (camphor-derived) ketones and pyridinylalkylamines catalyze the enantioselective Henry (nitro aldol) reaction between nitromethane and o-anisol in the presence of copper(II) acetate, wi

Synthesis of a camphor-derived auxiliary and the application to the asymmetric Darzens reaction

A readily available chiral camphor-derived auxiliary was synthesised through a highly efficient and short general route. The Darzens reaction of the auxiliary with aldehydes in the presence of base gave glycidic esters with almost complete diastereocontro

Facile synthesis of isocampholenic acids by the rearrangement of camphor derivatives

A variety of substituted isocampholenic acid derivatives were prepared by rearrangement of the camphor skeleton of a variety of tertiary alcohols derived from ketopinic acid. The reaction was highly reliable and retained the stereochemical information from the camphor scaffold. This rearrangement represents an efficient way to prepare synthetically useful isocampholenic acids. Mechanistic experiments show that a short-lived carbocation is implicated in the reaction.

Enantioselective addition of diethylzinc to aldehydes in the presence of chiral hydrazone and imine ligands

Optically active hydrazone and imine were found to act as effective ligands for enantioselective addition of diethylzinc to aldehydes. This reaction provided optically active secondary alcohols with ee up to 71%.

Exo-10,10-diphenyl-2,10-camphanediol as a new chiral auxiliary in asymmetric reduction

Stereoselective reduction of α-keto ester derived from exo-10,10- diphenyl-2,10-camphanediol with various hydrides proceeded with high diastereoselectivities (≥ 96% de) to afford the corresponding α-hydroxy ester with excellent yields. Change of reducing

Novel camphor-derived chiral auxiliaries: Significant solvent and additive effects on asymmetric reduction of chiral α-keto esters

Stereoselective reduction of various α-keto esters 5a-d derived from exo-10,10-diphenyl-2,10-camphanediol 4a and exo-10,10-diphenyl-10-methoxy-2- camphanol 4b is described. High to excellent diastereomeric excess (99% de) with good chemical yields is obtained. The sense of stereoselectivity as a function of C10 modification is remarkable. Further, in the case of 5d, both diastereomers of α-hydroxyl esters can be obtained with excellent optical purity by the appropriate choice of reaction conditions. The influence of the solvents and additives on the reaction course has been investigated.