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

New cis-N-alkyl-1,3-oxazolidin-2-ones were prepared in moderate to good yields via phosgenation of erythro-1,2-aminoalcohol monoesters, accompanied by formation of aziridine by-products. On the other hand, their regioisomers trans-N-alkyl-1,3-oxazolidin-2-ones were prepared regio- and stereoselectively in good yields by ring expansion of trans-N-alkyl aziridine-2-carboxylates.

GRAPHICAL ABSTRACT

Keywords:

• Amino alcohol monoesters
• aziridine-2-carboxylates
• 1,3-oxazolidin-2-one
• phosgenation

ACKNOWLEDGMENT

We thank N. Gabsi for interesting and valuable English discussions.

Notes

^a Yields refer to isolated chromatographically pure compounds.

^a Yields refer to isolated chromatographically pure compounds.