220307-12-0

Upstream product

• 220306-89-8 N-[(E)-(S)-1-((S)-sec-Butyl)-4-hydroxy-but-2-enyl]-4-methoxy-2,3,6-trimethyl-benzenesulfonamide 
• 220306-88-7 (E)-(4S,5S)-4-(4-Methoxy-2,3,6-trimethyl-benzenesulfonylamino)-5-methyl-hept-2-enoic acid methyl ester 
• 220306-87-6 N-((1S,2S)-1-Hydroxymethyl-2-methyl-butyl)-4-methoxy-2,3,6-trimethyl-benzenesulfonamide 
• 80745-07-9 4-methoxy-2,3,6-trimethylbenzenesulfonyl chloride 
• 24629-25-2 (S)-isoleucinol 
• 247200-35-7 Ethyl (4S,5S,2Z)-5-methyl-4-[(4-methoxy-2,3,6-trimethylphenylsulfonyl)amino]hept-2-enoate 
• 247200-40-4 (4S,5S,2Z)-5-Methyl-4-[(4-methoxy-2,3,6-trimethylphenylsulfonyl)amino]hept-2-en-1-ol 
• 220652-44-8 (4S,5S,2Z)-O-Methoxycarbonyl-5-methyl-4-[(4-methoxy-2,3,6-trimethylphenylsulfonyl)amino]hept-2-en-1-ol 
• 220306-90-1 Carbonic acid (E)-(4S,5S)-4-(4-methoxy-2,3,6-trimethyl-benzenesulfonylamino)-5-methyl-hept-2-enyl ester methyl ester 

Downstream Products

• 220307-15-3 (E)-3-[(2R,3S)-3-((S)-sec-Butyl)-1-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-aziridin-2-yl]-acrylic acid tert-butyl ester 

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.

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.