A New Synthesis of Optically Active trans β-Amino Alcohols by Asymmetric Ring-opening of Symmetrical Oxiranes

The asymmetric ring-opening of symmetrical oxiranes with aniline or trimethylsilyl azide is effectively catalyzed by zinc (2R,3R)-tartrate or cupric (2R,3R)-tartrate to give trans N-phenyl (β-amino alcohol or trans O-trimethylsilyl 2-azido alcohols in 17–52% ee. The latter azido products can be easily converted into optically active trans β-amino alcohols by two-step procedure.