280142-38-3

Upstream product

• 138812-17-6 N,N'-bis<(S)-1-phenylethyl>ethanediimine 

Downstream Products

• 205988-38-1 1(R),2(R)-di-[(S)-1-phenylethylamino]-1,2-diphenylethane 
• 314249-74-6 (E,E)-6(R),7(R)-di-[(S)-1-phenylethylamino]-1,3,9,11-dodecatetraene 
• 521310-11-2 N,N'-bis[((S)-1-phenylethyl)]-4(R),5(R)-di(1-ethenyl-2-propenyl)imidazolidine 
• 521310-13-4 N,N'-bis[((S)-1-phenylethyl)]-1(R),2(R)-diamino-3(S),6(R)-diethenylcyclohex-4-ene 
• 880517-61-3 (4R,5R)-1,3-bis[(1S)-1-phenylethyl]-4,5-bis(1-vinylprop-2-en-1-yl)-1,3,2-diazaphospholidine 2-oxide 
• 880517-67-9 (3aR,4R,7S,7aR)-1,3-Bis-((S)-1-phenyl-ethyl)-4,7-divinyl-1,3,3a,4,7,7a-hexahydro-benzo[1,3,2]diazaphosphole 2-oxide 

Relevant academic research and scientific papers

Asymmetric synthesis of 1,2-diamines by the addition of allylic zinc and magnesium reagents to N,N'-bis[(S)-1-phenylethyl)]ethanediimine

The diimine prepared by condensation of glyoxal trimer dihydrate with (S)-1-phenylethylamine underwent double addition of allylic zinc compounds (2-butenyl-, 2,4-pentadienyl-, 2-methyl-2-propenylzinc bromide) in THF generally at -78 °C, with allylic inversion. The newly formed stereocentres adjacent to the nitrogen atoms had prevalently the R configuration. Removal of the auxiliary from the secondary 1,2-diamines with concomitant hydrogenation of the C=C double bonds afforded the primary 1,2-diamines. The reaction with 3-methyl-2-butenylzinc bromide gave almost exclusively the α- amino imine from which the α-aminoaldehyde was obtained by hydrolysis. On the other hand, 3-methyl-2-butenylmagnesium chloride reacted at 0-20 °C to give the diamine with linear-chain substituents, owing to the reversibility of the organometallic addition.