187531-92-6

Basic information

• Product Name: (2R,3S)-3-methyl-N-(4-methylbenzenesulfonyl)-2-vinylaziridine
• Synonyms: (2R,3S)-3-methyl-N-(4-methylbenzenesulfonyl)-2-vinylaziridine
• CAS NO: 187531-92-6
• Molecular Weight: 237.323
• Mol File: 187531-92-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3S)-3-methyl-N-(4-methylbenzenesulfonyl)-2-vinylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-methyl-N-(4-methylbenzenesulfonyl)-2-vinylaziridine(187531-92-6)
• EPA Substance Registry System: (2R,3S)-3-methyl-N-(4-methylbenzenesulfonyl)-2-vinylaziridine(187531-92-6)

Safety Data

• Hazardous Substances Data: 187531-92-6(Hazardous Substances Data)

Upstream product

• 187531-93-7 (2R,3S)-3-Methyl-1-(toluene-4-sulfonyl)-aziridine-2-carbaldehyde 
• 159518-55-5 (3S)-Methyl-N-p-toluolsulfonylaziridin-(2R)-carbonsaeuremethylester 
• 153710-15-7 (2S,3S)-2-hydroxymethyl-3-methyl-1-<(4-methylphenyl)sulfonyl>aziridine 
• 183253-89-6 (2S,3S)-2-formyl-3-methyl-1-(toluene-4-sulfonyl)-aziridine 
• 19493-09-5 Methylenetriphenylphosphorane 
• 187531-94-8 (2S,3S)-3-methyl-N-(4-methylbenzenesulfonyl)-2-vinylaziridine 

Relevant articles and documents

A Thermodynamic Preference of Chiral N-Methanesulfonyl and N-Arenesulfonyl 2,3-cis-3-Alkyl-2-Vinylaziridines over Their 2,3-Trans-Isomers: Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (E)-Alkene Dipeptide Isosteres

Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.