169870-31-9

Upstream product

• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 167029-47-2 (2R,3R)-2-hydroxymethyl-1-(4-methylphenylsulfonyl)-3-phenylaziridine 
• 169870-32-0 methyl (4S,5R,2Z)-4,5-epimino-N-(4-methylphenyl)sulfonyl-5-phenylpent-2-enoate 

Relevant academic research and scientific papers

Palladium(0)-Catalyzed Isomerization Reactions of Aziridines Bearing an α,β-Unsaturated Ester Group: A Thermodynamic Preference for Chiral Alkyl (2E)-4,5-cis-4,5-Epimino-N-(alkyl- or arylsvdfonyl) 2-Enoates over the Other Three Stereoisomers

Palladium(0)-catalyzed reactions of five sets of four stereoisomeric 4,5-epimino-N-(methanesulfonyl) or -N-(arylsulfonyl) 2-enoates reveal that 4,5-cis-(2E)-isomers are thermodynamically more stable than other isomers, in accord with calculations. A highly stereoselective synthesis of (E)-alkene dipeptide isosteres having the desired stereochemistries from unwanted stereoisomeric 4,5-epimino-N-(arylsulfonyl) 2-enoates is also presented.

A thermodynamic preference of chiral cis-γ,δ-epimino-(E)-α,β-unsaturated esters over other stereoisomers: Synthetically useful Pd(0)-catalyzed equilibrated reactions of aziridines bearing an α,β-unsaturated ester group

A practical synthesis of chiral N-arylsulfonyl-cis-γ,δ-epimino-(E)-α,β-enoates, key intermediates for the synthesis of (E)-alkene dipeptide isosteres via Pd(0)-catalyzed equilibrated reactions, has been successfully achieved by exposing N-arylsulfonyl-γ,δ

SN2' Ring opening of aziridines bearing an α,β-unsaturated ester group with organocopper reagents. A new stereoselective synthetic route to (E)-alkene dipeptide isosteres

Regio- and stereo-selective synthesis of (E)-alkene dipeptide isosters has been successfully achieved by exposing both (E)- and (Z)-N-(4-methylphenyl)sulfonyl-γ,δ-epimino-α,β-enoates to organocopper reagents at -78 deg C for 30 min.