Boc 2 O‐Promoted Cascade Reactions of Thioepoxides: Unexpected Formation of Oxazolidinones Featuring a C5 Sulfur‐Modified Side Chain
Abstract
ABSTRACT A novel Boc 2 O‐promoted cascade transformation has been developed for the efficient one‐step synthesis of C5 sulfur‐substituted oxazolidin‐2‐ones from thioepoxy amines. This method enables simultaneous oxazolidinone ring construction and side‐chain sulfur incorporation via intramolecular cyclization, significantly improving synthetic step economy. Mechanistic studies, including NMR and x‐ray analysis, suggest a 5‐ exo ‐tet cyclization pathway consistent with Baldwin's rules. This strategy expands the synthetic utility of oxazolidinone scaffolds, offering access to medicinally relevant sulfur‐containing analogues with potential pharmacological applications.
Fields of Study & Subjects
Sulfur-Based Synthesis Techniques
Synthesis of heterocyclic compounds
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- Asian Journal of Organic Chemistry
- Publisher
- Wiley
- Volume
- 15
- Issue
- 2
- Publication date
- 31 January 2026
- Language
- EN