ChemInform Abstract: Stereoselective Synthesis of cis‐and trans‐3,4,5‐Trisubstituted‐1,3‐oxazolidin‐2‐one Derivatives from 1,2‐Amino Alcohol Monoesters and Aziridine‐2‐carboxylates.

Abstract

Stereoselective Synthesis of cis-and trans-3,4,5-Trisubstituted-1,3-oxazolidin--2-one Derivatives from 1,2-Amino Alcohol Monoesters and Aziridine-2-carboxylates. -New cis N-alkyl-1,3-oxazolidin-2-ones (III) are formed in good yields via phosgenation of erythro-1,2-aminoalcohol monoesters, accompanied by the formation of aziridine by-products. On the other hand, their regioisomer trans-forms (VI) are build regio-and stereoselectively by ring expansion of trans-N-alkyl aziridine-2-carboxylates (IV). -(KAABI, A.; BESBES*, R.; Synth. Commun. 45 (2015) 1, 111-118, http://dx.