Synthesis of R- and S-MDMA via nucleophilic ring-opening of homochiral N-tosylaziridines
Australian Journal of Chemistry July 11, 2023 Katie D. Lewis, Glenn A. Pullella, Han Chern Loh et al. 2 citations
Homochiral (R)- and (S)-3,4-methylenedioxymethamphetamine (MDMA) were prepared in six steps (each) from the chiral pool precursors d- and l-alanine, respectively. The key step, copper-catalysed regioselective ring-opening of an N-tosylaziridine with an aryl Grignard reagent, proceeded in high yield with complete regioselectivity. Elaboration was achieved with preservation of configurational...