@article{3c060855fa8c4034b31f52d68295a22f,
title = "Synthesis of R - and S -MDMA via nucleophilic ring-opening of homochiral N -tosylaziridines",
abstract = "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 integrity, affording R- and S-MDMA hydrochlorides with enantiopurities of >99.5%, as determined by enantioselective HPLC with fluorescence detection. Attempts to apply the synthetic methodology to the synthesis of the homochiral enantiomers of the α-phenyl analogue of MDMA (UWA-001) were thwarted by a switch in regioselectivity in the key step.",
keywords = "(R)- and (S)-3, 4-methylenedioxymethamphetamine, aziridine, chiral pool, enantiopurity determination, HPLC with fluorescence detection, nucleophilic ring-opening, organic chemical synthesis, R - and S -MDMA, X-ray crystal structure",
author = "Lewis, {Katie D.} and Pullella, {Glenn A.} and Loh, {Han Chern} and Skelton, {Brian W.} and Flematti, {Gavin R.} and Piggott, {Matthew J.}",
note = "Funding Information: The work described herein was funded, in part, by UWA Medicine Small Bequests, and The Ada Bartholomew Medical Research Trust. Emyria Ltd are gratefully acknowledged for their enthusiastic sponsorship of, and partnership in, our MDMA-inspired drug discovery program. Acknowledgements Publisher Copyright: {\textcopyright} 2023 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.",
year = "2023",
month = jul,
day = "12",
doi = "10.1071/CH23064",
language = "English",
volume = "76",
pages = "299--310",
journal = "Australian Journal of Chemistry",
issn = "0004-9425",
publisher = "CSIRO Publishing",
number = "5",
}