Synthetic and theoretical investigation on the one-pot halogenation of β-amino alcohols and nucleophilic ring opening of aziridinium ions.

ABSTRACT: Aziridinium ions are useful reactive intermediates for the synthesis of enantiomerically enriched building blocks. However, N,N-dialkyl aziridinium ions are relatively underutilized in the synthesis of optically active molecules as compared to other three-membered ring cogeners, aziridines and epoxides. The characterization of both optically active aziridinium ions and secondary β-halo amines as the precursor molecules of aziridinium ions has been scarcely reported and is often unclear. In this paper, we report for the first time the preparation and experimental and theoretical characterization of optically active aziridinium ions and secondary β-halo amines. Optically active secondary N,N-substituted β-halo amines were efficiently synthesized from N,N-substituted alaninol via formation an

SUBMITTER: Chen Y 

PROVIDER: S-EPMC6324733 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature