187532-12-3

Upstream product

• 187532-10-1 (3R,4S)-5-methyl-4-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-1-hexen-3-ol 
• 220652-42-6 (4S,2Z)-O-Methoxycarbonyl-5-methyl-4-[(2,4,6-trimethylphenylsulfonyl)amino]hex-2-en-1-ol 
• 220306-79-6 Carbonic acid methyl ester (E)-(S)-5-methyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-hex-2-enyl ester 
• 220306-83-2 Methanesulfonic acid (E)-(S)-5-methyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-hex-2-enyl ester 
• 148838-43-1 N-((S)-1-Formyl-2-methyl-propyl)-2,4,6-trimethyl-benzenesulfonamide 
• 247200-33-5 Ethyl (4S,2Z)-5-methyl-4-[(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate 
• 247200-38-0 (4S,2Z)-5-Methyl-4-[(2,4,6-trimethylphenylsulfonyl)amino]hex-2-en-1-ol 
• 139192-50-0 (2S)-N-(2,4,6-trimethylbenzenesulfonyl)-2-amino-3-methyl-butanol 
• 187532-09-8 (3S,4S)-5-methyl-4-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-1-hexen-3-ol 
• 220306-69-4 (E)-(S)-5-Methyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-hex-2-enoic acid methyl ester 
• 220306-75-2 N-((E)-(S)-4-Hydroxy-1-isopropyl-but-2-enyl)-2,4,6-trimethyl-benzenesulfonamide 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 2026-48-4 (S)-valinol 

Downstream Products

• 189291-24-5 (E)-3-[(2S,3S)-3-Isopropyl-1-(2,4,6-trimethyl-benzenesulfonyl)-aziridin-2-yl]-acrylic acid tert-butyl ester 
• 477781-25-2 N-[(1S,2R)-2-((S)-Hydroxy-phenyl-methyl)-1-isopropyl-but-3-enyl]-2,4,6-trimethyl-benzenesulfonamide 
• 189291-18-7 (E)-3-[(2R,3S)-3-Isopropyl-1-(2,4,6-trimethyl-benzenesulfonyl)-aziridin-2-yl]-acrylic acid tert-butyl ester 
• 189291-22-3 Methyl (2Z,4S,5S)-6-methyl-4,5-[N-(2,4,6-trimethylphenylsulfonyl)epimino]hept-2-enoate 
• 189291-20-1 Methyl (2E,4S,5S)-6-methyl-4,5-[N-(2,4,6-trimethylphenylsulfonyl)epimino]hept-2-enoate 
• 187532-11-2 (2R,3S)-3-Isopropyl-N-(2,4,6-trimethylphenylsulfonyl)-2-vinylaziridine 

Relevant academic research and scientific papers

Selective synthesis of cis-2-vinyl-3-alkylaziridines and 3-pyrrolines from common intermediates (Z)-4-N-arylsulfonylaminoalk-2-en-1-ols

A simple method for the synthesis of both cis-2-vinylaziridines and 3-pyrrolines from common intermediate (Z)-4-(N-arylsulfonyl)amino-4-alkylbut-2-en-1-ols, is described. Palladium(0)-catalyzed reactions of methyl carbonates of the N-protected (Z)-4-amino-4-alkylbut-2-en-1-ols yield predominantly cis-3-alkyl-2-vinylaziridines. Alternatively, upon exposure to sodium hydride, methanesulfonates derived from N-protected (Z)-4-amino-4-alkylbut-2-en-1-ols give exclusively the corresponding 3-pyrrolines in high yields. A synthesis of biologically important (S)-3,4-dehydroproline is also presented.

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.