Science of Synthesis

Rück-Braun, K.; Freysoldt, T., Science of Synthesis, (2007) 35, 757.

General Introduction

β-Iodoamines are important synthetic intermediates, and may be synthesized by the ring opening of aziridines. A careful choice of substrate, reaction conditions, and reagents is required. Most substrates require acidic conditions, such that acid-labile groups are not tolerated. Nevertheless, as the reaction proceeds mostly via an SN2 mechanism, excellent diastereo- and regioselectivity can be achieved. Attack of the nucleophile at the more hindered carbon atom leads to the formation of products with an anti configuration. Also, electron-withdrawing groups on the nitrogen atom enhance the reactivity of the aziridine toward ring opening.

Meeee eeee ee eee eeeeeeeeee eeeeeeee ee eeee eeeeeee ee eeeeeeeee eeee eee eeeeeeeeeeeeeeee ee eeeeeeeee eeee eeeeeee, eeeeeeeeeeeeee eeeeeeee eee eeee eeee ee eeeeeee eeeeeee ee eeeeeeee eee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeee eeeeee eeeeeee. Mee eeeeee eee ee eeee ee eeee eeee eeee eeee eee eeeeeeeeeee eeeee eee eee ee eeeeeeeeeeeeeeee eeee eeeeeeee ee (ee e eee eeeee) eee eeeeeeeee eeeeeeeeee.