Symmetrical and unsymmetrical N,N'-piperazine derivatives of (-)-norephedri
ne and o-aminophenol were synthesized stereoselectively in yields >70% by r
eduction of the corresponding N,N'-ethylenebisoxazolidine heterocycles. The
stereochemistry at the ring fusion carbons was established by NMR spectros
copy and X-ray crystallography. (C) 1999 Elsevier Science Ltd. All rights r
eserved.