187532-00-9

Basic information

• Product Name: (2S,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine
• Synonyms: (2S,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine
• CAS NO: 187532-00-9
• Molecular Weight: 341.474
• Mol File: 187532-00-9.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine(187532-00-9)
• EPA Substance Registry System: (2S,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine(187532-00-9)

Safety Data

• Hazardous Substances Data: 187532-00-9(Hazardous Substances Data)

Upstream product

• 220306-86-5 Methanesulfonic acid (E)-(S)-5-phenyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-pent-2-enyl ester 
• 220306-82-1 Carbonic acid methyl ester (E)-(S)-5-phenyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-pent-2-enyl ester 
• 187531-98-2 (3R,4S)-5-phenyl-4-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-1-penten-3-ol 
• 99113-30-1 ((1S,2R)-1-benzyl-2-hydroxybut-3-enyl)carbamic acid tert-butyl ester 
• 132273-11-1 (4S,3R)-4-amino-5-phenyl-pent-1-en-3-ol 
• 220306-74-1 (E)-(S)-5-Phenyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-pent-2-enoic acid methyl ester 
• 220306-78-5 N-((E)-(S)-1-Benzyl-4-hydroxy-but-2-enyl)-2,4,6-trimethyl-benzenesulfonamide 
• 220324-31-2 N-((S)-1-Formyl-2-phenyl-ethyl)-2,4,6-trimethyl-benzenesulfonamide 
• 182880-90-6 (S)-N-(2,4,6-trimethylphenylsulfonyl)phenylalaninol 
• 3182-95-4 L-Phenylalaninol 
• 773-64-8 2-mesitylenesulphonyl chloride 

Downstream Products

• 187531-99-3 (2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine 
• 189291-26-7 tert-butyl (4R,5S,2E)-4,5-epimino-6-phenyl-N-[(2,4,6-trimethylphenyl)sulfonyl]hex-2-enoate 
• 196958-80-2 (E)-3-[(2S,3S)-3-Benzyl-1-(2,4,6-trimethyl-benzenesulfonyl)-aziridin-2-yl]-2-methyl-acrylic acid methyl ester 
• 189291-28-9 tert-butyl (4S,5S,2E)-4,5-epimino-6-phenyl-N-[(2,4,6-trimethylphenyl)sulfonyl]hex-2-enoate 

Relevant articles and documents

Selective synthesis of nonracemic 3-pyrrolines and 2,3-cis-2-vinylaziridines from (z)-amino allylic alcohols: a new synthetic route to chiral 3,4-dehydroproline

Both nonracemic 3-pyrrolines and 2,3-cis-2-vinyIaziridines have been synthesized selectively from common (Z)-allylic alcohols by simply changing the leaving group and the reaction conditions. Whereas treatment of (Z)-allylic mesylates with NaH yields exclusively 3-pyrrolines in high yields, exposure of allylic methyl carbonates to a catalytic amount of Pd(PPh3)4 affords 2,3-cw-2-vinylaziridines diastereoselectively in high yields. A simple synthesis of (5)-3,4-dehydroproline starting from (/?)-serine is also described. Thieme Stuttgart.

A 2,3-cis-selective synthesis of aziridines bearing a vinyl group from allyl methyl carbonates and allyl mesylates

A convenient method for the synthesis of synthetically useful chiral 2-vinylaziridines from natural α-amino acids is described. Satisfactory 2,3-cis-selectivities are obtained by exposure of methyl carbonates of various allylic alcohols bearing an N-protected amino group to a catalytic amount of tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4, in aprotic solvents such as THF. Base-promoted aziridination of mesylates of various N-protected amino allylic alcohols followed by Pd(PPh3)4 catalyzed isomerization for the 2,3-cis-selective synthesis of vinylaziridines is also presented.

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.