508183-97-9Relevant academic research and scientific papers
Chiral glycine cation equivalents: N-acyliminium species derived from diketopiperazines
Bull, Steven D.,Davies, Stephen G.,Garner, A. Christopher,O'Shea, Michael D.,Savory, Edward D.,Snow, Emma J.
, p. 2442 - 2448 (2002)
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.
