220652-32-4

Upstream product

• 220324-30-1 N-((S)-1-Formyl-3-methyl-butyl)-4-methyl-benzenesulfonamide 
• 247200-36-8 Ethyl (4S,2Z)-6-methyl-4-[(4-methylphenylsulfonyl)amino]hept-2-enoate 
• 124-63-0 methanesulfonyl chloride 
• 247200-41-5 (4S,2Z)-6-Methyl-4-[(4-methylphenylsulfonyl)amino]hept-2-en-1-ol 

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.