title: Novel stereoselective synthesis of functionalized oxazolidinones from chiral aziridines.
abstract: Enantiomerically pure N-(R)-alpha-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 alpha-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.
authors.affiliation: Department of Chemistry, Sogang University, Seoul, Korea.
authors.forename: Chan Sun
authors.initials: CS
authors.lastname: Park
authors.forename: Min Sung
authors.initials: MS
authors.lastname: Kim
authors.forename: Tae Bo
authors.initials: TB
authors.lastname: Sim
authors.forename: Do Kyu
authors.initials: DK
authors.lastname: Pyun
authors.forename: Cheol Hae
authors.initials: CH
authors.lastname: Lee
authors.forename: Daeock
authors.initials: D
authors.lastname: Choi
authors.forename: Won Koo
authors.initials: WK
authors.lastname: Lee
authors.forename: Jae-Won
authors.initials: JW
authors.lastname: Chang
authors.forename: Hyun-Joon
authors.initials: HJ
authors.lastname: Ha