Stereoselective Synthesis of 4,5-Disubstituted Oxazolidin-2-ones via Tandem Lossen Rearrangement and Ring Closure of Asymmetric Aldol Adducts
Abstract
An efficient and stereoselective approach for the synthesis of 4,5-disubstituted oxazolidin-2-ones has been developed via a tandem Lossen rearrangement/ring-closure sequence from asymmetric aldol adducts. This transformation proceeds under mild conditions with broad functional group compatibility, enabling access to all four possible 4,5-stereoisomers with excellent diastereocontrol. The synthetic utility of this methodology is demonstrated in concise syntheses of the bioactive compounds (-)-cytoxazone and linezolid in three and seven steps, respectively.
Fields of Study & Subjects
Microbial Natural Products and Biosynthesis
Asymmetric Synthesis and Catalysis
Synthetic Organic Chemistry Methods
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 2
- Pages
- 1209–1214
- Publication date
- 1 January 2026
- Language
- EN