Stereoselective synthesis of cyclopropane-1,2-bis(glycine) derivatives

Article abstract of DOI:10.1016/S0040-4020(97)00657-1

Conformationally constrained bis(glycines) as trans derivatives of cyclopropane have been prepared in stereoselective syntheses. (S)-4-Benzyl-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[3.1.0]hex-3-one derivative. X-ray data for the latter and for (1S,2S)-1,2-bis{(1S)-azido-2-oxo-2[(4S)-benzyl-2-oxo-3-oxazolidinyl] -ethyl}cyclopropane are presented.