Stereospecific synthesis of Pd(0)-catalyzed oxazolidinone with tetracyclic structure
The efficient synthesis of a new class of oxazolidinone with strained rings is described. The allylic cis-diol as the key intermediate was first prepared via two steps starting from p-benzoquinone. Formation of the bis-carbamate groups with p-TsNCO of allylic cis-diol followed by a Pd(0) catalyzed ionization/cyclization reaction gave the corresponding oxazolidinone derivative. Oxidation and acetylation of only one alkene moiety in the compound gave a diacetate oxazolidinone compound stereoselectively. The structure of diacetate oxazolidinone compound was resolved by X-ray diffraction and the stereochemistry of the structure was determined. Characterization of all the synthesized compounds was performed by FT-IR, H-1 NMR, C-13 NMR, and Elemental Analysis techniques.
- Journal
- SYNTHETIC COMMUNICATIONS
- Year
- 2023
- Volume
- 53
- Issue
- 21
- Pages
- 1832-1843
- ISSN
- 0039-7911
- eISSN
- 1532-2432
- DOI
- 10.1080/00397911.2023.2252537
- WoS UID
- WOS:001060070100001