Asymmetric synthesis of β-aminotetralins by electrophilic amination

Article abstract of DOI:10.1016/S0040-4020(01)85702-1

An effective synthesis of β-aminotetralins (6) including an asymmetric electrophlic amination by di-t-butyl azodicarboxylate is reported. Depending on the chiral auxiliaries (S)-7a-d, the central intermediates 9 and 10 could be isolated in 62-80% de. Subsequent hydrolysis and reductive degradation resulted in the nonracemic final products 6 (57-84% ee). Separation of the diastereomeric intermediates by chromatography makes possible the synthesis of optically pure products. An induction model for the asymmetric amination is provided.