78342-49-1

Upstream product

• 78342-45-7 (2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(3-phenyl-2-propyn-1-yl)pyrazine 
• 78342-46-8 (2R,5S)-5-isopropyl-3,6-dimethoxy-2-propargyl-2,5-dihydropyrazine 
• 591-50-4 iodobenzene 
• 71460-02-1 methyl (2S)-2-(tert-butoxycarbonylamino)pent-4-ynoate 
• 848132-12-7 methyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-phenyl-4-pentynoate 

Downstream Products

• 848132-13-8 methyl (2S)-5-phenyl-3,4-dihydro-2H-2-pyrrolecarboxylate 
• 153242-44-5 methyl (2S,5R)-5-phenyltetrahydro-2H-2-pyrrolecarboxylate 

Relevant academic research and scientific papers

Novel approach to 5-substituted proline derivatives using a silver-catalyzed cyclization as the key step

(Chemical Equation Presented) A novel synthetic approach to the synthesis of enantiomerically pure 2,5-disubstituted pyrrolines is described. The methodology involves a Ag-catalyzed 5-endo-dig cyclization of enantiopure aryl-substituted acetylene-containi

Stereoselective synthesis of alkynylglycines and α,α′-alkynyl-bridged bis(glycines)

Pd-CuI catalysis has been used to effect carbo-substitution with iodoarenes on the terminal alkynyl carbon in (25,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-propargylpyrazine. Bridged structures were formed from diiodoarenes. Homocoupling with bridge for

ENANTIOSELECTIVE SYNTHESIS OF NON-PROTEINOGENIC AMINO ACIDS VIA METALLATED BIS-LACTIM ETHERS OF 2,5-DIKETOPIPERAZINES

Bis-lactim ethers 1 of 2,5-diketopiperazines contain a chiral inducing center, an acidic CH-bond and two sites susceptible to hydrolysis.They react with BuLi to give Li compounds of type 4, 15, 29 or 32, which possess a prochiral C atom.They readily add electrophiles (such as alkylating agents or carbonyl compounds) with unusually high diastereoface differentiation.In many cases the d.e-value (d.e. = diastereomeric excess = asymmetric induction) of the adduct exceeds 95percent.On hydrolysis the adducts are cleaved liberating the chiral auxiliary (used to build up the bis-lactim ether 1) and the target molecules, the optically active amino acid methyl esters of type 8, 19, 25 or 36.The two amino acid esters are separable either by fractional distillation or (eventually after further hydrolysis to amino acids) by chromatography.Transition state models are discussed that could explain the exceptionally high asymmetric induction and the predictability of the induced configuration.