Novel Stereoselective Synthesis of Functionalized Oxazolidinones from Chiral Aziridines

Abstract

Enantiomerically pure N-(R)-α-methylbenzyl-4(R)-(chloromethyl)oxazolidinones (4R)-5a−k were synthesized in one step and high yields from various aziridine-2-methanols (S)-2a−k by intramolecular cyclization with phosgene. The α-methylbenzyl substituent on the nitrogen was easily cleaved to give both enanatiomers of 4-(chloromethyl)oxazolidinones (R)-7a and (S)-7a. (R)-7a was used for the efficient syntheses of (l)-homophenylalaninol analogues (S)-12a−j. We also applied the same methodology to prepare oxazolidinones 9a−c containing a heteroatom-substituted alkyl group at C-4 in high yields.