Several pathways leading to ethyl α-azido-α-alkenoates (8) by the β-elimination to ethyl α-azido-β-substituted (hydroxy-, acetoxy-, or mesyloxy)-alkanoates with NaN3 or Et3N have been examined. The optimized procedure, in combination with subsequent reduction provides a general synthetic route to α-amino-α-alkenoic acid esters (9). The configuration of 8 and 9 have been shown to be of (Z)-geometry.
Die aus den (E)‐Alkenoaten (I) zugänglichen Bromhydrine (II) werden zu den Derivaten (III) acetyliert, die beim Behandeln mit NaN3/HMPT in die ungesättigten Azidoester (Z)‐(IV) übergehen; die Azide (Z)‐(IV) werden zu den Aminen (Z)‐(V) reduziert, die als Chloracetamide (Z)‐(VI) charakterisiert werden.
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