title: Origins of selectivity in Brønsted acid-promoted diazoalkane-azomethine reactions (the aza-Darzens aziridine synthesis).
abstract: The mechanism of the Brønsted acid-catalyzed aza-Darzens reaction is explored by charting the stereochemical outcome of the triflic acid-promoted conversion of trans-triazolines to cis-aziridines. These experiments are consistent with the intermediacy of an α-diazonium-β-amino ester intermediate.
authors.affiliation: Department of Chemistry & Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, United States.
authors.forename: Timothy L
authors.initials: TL
authors.lastname: Troyer
authors.forename: Hubert
authors.initials: H
authors.lastname: Muchalski
authors.forename: Ki Bum
authors.initials: KB
authors.lastname: Hong
authors.forename: Jeffrey N
authors.initials: JN
authors.lastname: Johnston