Science of Synthesis

Rück-Braun, K.; Freysoldt, T., Science of Synthesis, (2007) 35, 527.

General Introduction

Ring opening of aziridines leads to 2-nitrogen-functionalized bromoalkanes which are important synthetic intermediates. By a careful choice of the substituents, as well as the brominating reagent and the reaction conditions, excellent stereo- and regioselectivity can be achieved. If the reaction proceeds via an SN1 route, ring opening at the less hindered carbon is sterically favored, and mixtures of diastereomers are observed. Attack at the least hindered carbon atom and the resulting anti configuration of the products is also observed when an SN2 route is preferred. The presence of electron-withdrawing groups on the nitrogen enhances the reactivity of the aziridine toward ring opening (‌Scheme 1‌). Previously published information on the ring opening of aziridines to give bromoalkanes can be found in Houben–Weyl, Vol. 5/4, p 433 and Vol. 11/2, p 248.

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