Abstract

A practical and selective method for the synthesis of the β-arylamines 5 and the cis- or trans-amino alcohols 8 or 11 is reported. The reaction sequence starts from α-tetralones 1 which readily react with dibenzyl azodicarboxylate to afford the protected α-hydrazino ketones 2. Then, depending on the reduction conditions, the trans-hydrazino alcohols 10 or the cis isomers 7 are formed predominantly. The stereoselectivities which range between 18:1 and 1:67 (trans/cis) are explained by stereoelectronic effects (σ,σ interactions) and steric hindrance. Depending on the workup procedure, we can control, whether the cis-hydrazino alcohols 7 or the oxazolidinone derivatives 3 are isolated. Subsequent hydrogenolyses of 4, 7 and 10 lead to the target molecules 5, 8 and 11, respectively.

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