126255-88-7

Upstream product

• 126255-78-5 N,N'-Fumaroylbis((S)-prolin-benzylester) 
• 542-92-7 cyclopenta-1,3-diene 
• 126255-78-5 N,N'-Fumaroylbis<(S)-prolin-benzylester> 

Downstream Products

• 126255-93-4 N-<(1R,4S,6S,8R,9S)-2-Oxo-3-oxatricyclo<4.2.1.0^4,8>non-9-ylcarbonyl>-(S)-prolin-benzylester 
• 126255-92-3 (S)-1-((1S,3S,6R,7R,9S)-2-Iodo-5-oxo-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carbonyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 126255-92-3 N-<(1R,4S,5S,6S,8R,9S)-5-Iod-2-oxo-3-oxatricyclo<4.2.1.0^4,8>non-9-ylcarbonyl>-(S)-prolin-benzylester 

Relevant academic research and scientific papers

Amino Acid Esters as Chiral Auxiliaries in Lewis Acid Catalyzed Diels-Alder Reactions

Cylopentadiene, cyclohexadiene and alkyl-substituted butadienes react with N-acryloyl-, N-crotonoyl- and N-(4-nitrocinnamoyl)-(S)-proline benzyl and allyl ester in the presence of Lewis acids to give the cycloadducts in high yields and with stereoselectiv

Thermal Diels-Alder Reactions with N-(2-Alkenoyl)-(S)-proline Esters as Chiral Dienophils

Cyclopentadiene reacts with N-acryloyl-(S)-proline benzyl and allyl ester in toluene at 0 deg C to give the bicycloheptenecarboxylic acid amides with a stereoselection of (2S):(2R) = 81:19.In the reactions with the N,N'-fumaroylbis(proline esters) the cycloadducts are formed in high yields and with isomer ratios of up to 97:3.The absolute configuration of N,N'-hept-5-ene-2,3-diyldicarbonyl>bis- (6a) has been determined by an X-ray analysis.In the reactions of the acrylamides with cyclopentadiene and of the furmaramides with cyclopentadiene, isoprene and 2,3-dimethylbutadiene the use of water/ethanol mixtures as solvent, if indicated in the presence of detergents, doubles the yields.However, a positive influence of the aqueous medium on the diastereomeric ratio can not be observed.

ON THE ENHANCEMENT OF STEREOSELECTION BY COOPERATION BETWEEN CHIRAL AUXILIARIES. ASYMMETRIC DIELS-ALDER REACTIONS WITH FUMARIC ACID BIS((S)-PROLINE BENZYL ESTER) AMIDE

Fumaric acid bis((S)-proline benzyl ester) amide reacts with cyclopentadiene in thermal and Lewis acid catalyzed Diels-Alder reactions to give cycloadducts with high yields and diastereomeric ratios up to 100:1.