Abstract
Aziridines are important synthetic intermediates which readily undergo ring-opening reactions. It is demonstrated that electron-rich phosphines are efficient catalysts for the regioselective rearrangement of N-acylaziridines to oxazolines. The reactions occur in excellent yield under neutral conditions. Evidence is provided for an addition/elimination mechanism by generation of a phosphonium intermediate. Similar intermediates may be useful for the development of alternate aziridine ring-opening processes and stereoselective synthesis with enantiopure phosphines.
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