70190-87-3

Upstream product

• 1200-88-0 norbornene-5,6-dicarboxylic acid 
• 929108-82-7 (1S,2S,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-((R)-1-anthracen-9-yl-2,2,2-trifluoro-ethyl) ester 

Downstream Products

• 5826-29-9 (1R,2R,3R,6S,7S,9S)-2-Hydroxy-5-oxo-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid methyl ester 
• 196503-51-2 (1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid 
• 198223-93-7 (1S,2S,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-[((S)-2-hydroxy-1-phenyl-ethyl)-amide] 
• 952117-59-8 1-benzyl-6-methyl-[(4R,5S,6S,7S)-5-cyano-3-formyl-4,5,6,7-tetrahydro-4,7-methano-2H-isoindole-1,6-dicarboxylate] 
• 196503-55-6 1-benzyl-6-methyl-[(4R,5S,6S,7S)-5-carbamoyl-4,5,6,7-tetrahydro-4,7-methano-2H-isoindole-1,6-dicarboxylate] 
• 196503-53-4 (-)-(1R,2R,3R,6S,7S,9R)-5-oxo-2-exo-(phenylsulfonyl)-4-oxatricyclo[4.2.1.0^3,7]nonane-9-exo-carboxamide 
• 196503-54-5 (1S,2S,3R,4R)-5-Benzenesulfonyl-3-carbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 
• 196503-52-3 (1R,2R,3R,6S,7S,9R)-5-Oxo-2-phenylsulfanyl-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid amide 

Relevant academic research and scientific papers

Di-2,2,2-trifluoro-1-(9-anthryl)ethyl fumarate, an easy starting point for the enantioselective preparation of trans-cyclohexene-4,5-dicarboxylate derivatives by Diels-Alder reaction

Di-2,2,2-trifluoro-1-(9-anthryl)ethyl fumarate has been synthesized from fumaric acid and enantiopure Pirkle alcohol. The Diels-Alder reaction with different dienes employing different reaction conditions was assayed, with high diastereomeric excesses obtained. The structure and geometry of the cycloadducts was analyzed by NMR, molecular mechanics and X-ray diffraction. Hydrolysis made it possible to obtain the enantioenriched trans-cyclohexene-4,5-dicarboxylate derivatives and allow us to recover chiral auxiliary.

Resolution of (±)-Bicyclo[2.2.1]hept-5-ene-trans-2,3-dicarboxylic Acid: Crystal Structure of Its Cinchoninium Salt

Abstract: Single crystals of (+)-cinchoninium (+)-bicyclo[2.2.1]hept-5-ene-trans-2-carboxyl-3-carboxylate (S,S)-2 were obtained upon resolution of racemic (±)-bicyclo[2.2.1]hept-5-ene-trans-2,3-dicarboxylic acid rac-1 with (+)-cinchonine. An X ray diffraction analysis established the most important secondary interactions between the ions that are deemed responsible for the diastereomeric separation process. From (S,S)-2 enantiomerically pure (+)-bicyclo[2.2.1]hept-5-ene-trans-2,3-dicarboxylic acid (S,S)-1 was isolated in 72 % yield. Graphical Abstract: An X-ray diffraction analysis of (+)-cinchoninium (+)-bicyclo[2.2.1]hept-5-ene-trans-2-carboxyl-3-carboxylate (S,S)-2 established the most important secondary interactions between the ions that are deemed responsible for the diastereomeric separation process.[Figure not available: see fulltext.]

Chiral rhodium-diphosphine catalyst capable of catalytic reduction of a tetramisole precursor to give a significant excess of the desired S-(-)isomer, levamisole

A soluble, chiral, rhodium-containing catalyst which permits the catalytic reduction of prochiral 3-acyl-1-(2-alkoxyethyl)-4-phenyl-2-imidazolinones to chiral 3-acylimidazolidinones with a substantial excess of the desired S optical isomer. The 3-acylimidazolidinones may in turn be substantially converted to levamisole, and S isomer of tetramisole. The resolution of tetramisole to remove the R isomer is thus avoided.