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DOI: 10.1055/sos-SD-035-00624

Rück-Braun, K.; Freysoldt, T.Science of Synthesis, (200735757.

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.

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