Collect. Czech. Chem. Commun. 2009, 74, 1069-1080
Published online 2009-07-10 20:35:38

Addition of lithiated methoxyallene to aziridines – a novel access to enantiopure piperidine and β-amino acid derivatives

Vladimir Prisyazhnyuk, Matthias Jachan, Irene Brüdgam, Reinhold Zimmer and Hans-Ulrich Reissig*

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, D-14195 Berlin, Germany


Addition of lithiated methoxyallene to aziridine derivatives provided the expected primary addition products. The less substituted carbon of the aziridine ring was attacked selectively. The primary adducts could be converted to enantiopure piperidine derivatives or β-amino acid derivatives. The unexpected reactions lead to a tricyclic sulfonamide and to alkynyl-substituted aminoethers. The efficient two-step conversion of a piperidone derivative to a benzomorphan demonstrates the potential of this approach to biologically active compounds.

Keywords: Allenes; Aziridines; Alkynes; Piperidones; Benzomorphan; β-Amino ester.

References: 79 live references.