508183-95-7

Upstream product

• 108-24-7 acetic anhydride 
• 508183-93-5 (3S,6R)-N,N'-bis(p-methoxybenzyl)-6-hydroxy-3-isopropylpiperazine-2,5-dione 
• 1027973-78-9 3-isopropyl-1,4-bis-(4-methoxy-benzyl)-5-trimethylsilanyloxy-3,4-dihydro-1H-pyrazin-2-one 
• 508183-97-9 (5S)-N,N'-bis(p-methoxybenzyl)-5-isopropylpiperazine-2,3,6-trione 
• 205517-34-6 (3S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-piperazine-2,5-dione 
• 127-09-3 sodium acetate 

Relevant academic research and scientific papers

Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines

Studies towards a N,N′-bis(p-methoxybenzyl)diketopiperazine asymmetric glycine cation equivalent for the synthesis of homochiral α-amino acids are described. The oxidation of enolate 3 with molecular oxygen provides either a mixture of hydroxylated diketopiperazines 7 and 8 or trione 10 depending upon the reaction conditions. The nucleophilic reduction of trione 10 and the reaction of acetoxy N-acyliminium ion precursors 5 and 6, derived from 7 and 8, with allyltrimethylsilane and boron trifluoride etherate is examined and a model for the stereoselectivity observed in these additions is presented.