220324-31-2

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 182880-90-6 (S)-N-(2,4,6-trimethylphenylsulfonyl)phenylalaninol 

Downstream Products

• 220306-86-5 Methanesulfonic acid (E)-(S)-5-phenyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-pent-2-enyl ester 
• 220652-34-6 Methanesulfonic acid (Z)-(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 
• 220652-46-0 Carbonic acid methyl ester (Z)-(S)-5-phenyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-pent-2-enyl ester 
• 220306-78-5 N-((E)-(S)-1-Benzyl-4-hydroxy-but-2-enyl)-2,4,6-trimethyl-benzenesulfonamide 
• 187532-00-9 (2S,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine 
• 187531-99-3 (2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine 
• 678166-38-6 (4S,2E)-O-methoxycarbonyl-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol 
• 678166-52-4 (4S,2E)-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-O-methylsulfonylpent-2-en-1-ol 
• 678166-33-1 (4S,2E)-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol 
• 678166-27-3 methyl (4S,2E)-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-enoate 

Relevant academic research and scientific papers

Stereodivergent synthesis of chiral 2-alkenylaziridines: Palladium(0)-catalyzed 2,3-cis-selective aziridination and base-mediated 2,3-trans-selective aziridination

Whereas treatment of the allylic mesylates of N-protected 2-alkyl-4-amino-(E)-2-alken-1-ols with sodium hydride in DMF yields exclusively the corresponding thermodynamically less stable 2,3-trans-2-alkenyl-3- alkylaziridines, exposure of the methyl carbon

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.