STEREOSELECTIVE SYNTHESIS OF CYCLOPROPANE-1,2-BIS(GLYCINE) DERIVATIVES

Conformationally constrained bis(glycines) as trans derivatives of cyc lopropane have been prepared in stereoselective syntheses. (S)-4-Benzy l-2-oxazolidinone was used as a chiral auxiliary, trisyl azide was the electrophilic source of amine nitrogen. Four stereogenic centers were created. A related cis-cyclopropane derivative suffered ring closure with Formation of a bicyclo[3.1.O]hex-3-one derivative. X-ray data For the latter and for S)-benzyl-2-oxo-3-oxazolidinyl]-ethyl}cyclopropane are presented. (C) 1997 Elsevier Science Ltd.