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)-MDMA were synthesized in six steps from d- and l-alanine. A copper-catalyzed regioselective ring-opening of an N-tosylaziridine with an aryl Grignard reagent gave high yields and complete regioselectivity. The synthesis preserved configurational integrity, yielding R- and S-MDMA hydrochlorides with enantiopurities greater than 99.5%, confirmed by enantioselective HPLC with fluorescence detection. Applying the same method to make homochiral enantiomers of the α-phenyl analogue UWA-001 failed due to a switch in regioselectivity in the key step.