CAN-Promoted Boc2O‑Mediated Cascade Conversion of Aziridines to Oxazolidinones
- 1Department of Chemistry, National Chung Hsing University, 145 Xingda Rd., South Dist., Taichung City 402, Taiwan
Abstract
An efficient CAN-promoted Boc2O-mediated cascade conversion of aziridines to oxazolidinones has been developed. The transformation proceeds under mild, CO2-free conditions and provides structurally diverse oxazolidinones in 16–99% yields (46 examples), with gram-scale reactions demonstrating its synthetic practicality. Boc2O serves as an alternative carbonyl source and is proposed to generate a reactive tert-butyl carbonate species that undergoes nucleophilic aziridine ring opening followed by intramolecular cyclization. Control experiments identify CAN as the most effective promoter examined and demonstrate that DBU and TBAB cooperatively enhance reaction efficiency. Stereochemical studies are consistent with an SN2-type ring-opening pathway. This methodology provides a practical complement to existing CO2-based approaches and expands the synthetic utility of Boc2O-mediated cascade chemistry.
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BibTeX
@article{huang2026canpromoted,
title = {{CAN-Promoted Boc2O‑Mediated Cascade Conversion of Aziridines to Oxazolidinones}},
author = {Yu-Jin Huang and Meng-Hsia Tsai and Xin-Ni Zhan and Po-Wei Wu and Cheng-Kun Lin},
journal = {The Journal of Organic Chemistry},
year = {2026},
month = oct,
doi = {10.1021/acs.joc.6c01591},
url = {https://doi.org/10.1021/acs.joc.6c01591},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - CAN-Promoted Boc2O‑Mediated Cascade Conversion of Aziridines to Oxazolidinones
AU - Yu-Jin Huang
AU - Meng-Hsia Tsai
AU - Xin-Ni Zhan
AU - Po-Wei Wu
AU - Cheng-Kun Lin
PY - 2026
DA - 2026/10/08
JO - The Journal of Organic Chemistry
DO - 10.1021/acs.joc.6c01591
UR - https://doi.org/10.1021/acs.joc.6c01591
AB - An efficient CAN-promoted Boc2O-mediated cascade conversion of aziridines to oxazolidinones has been developed. The transformation proceeds under mild, CO2-free conditions and provides structurally diverse oxazolidinones in 16–99% yields (46 examples), with gram-scale reactions demonstrating its synthetic practicality. Boc2O serves as an alternative carbonyl source and is proposed to generate a reactive tert-butyl carbonate species that undergoes nucleophilic aziridine ring opening followed by intramolecular cyclization. Control experiments identify CAN as the most effective promoter examined and demonstrate that DBU and TBAB cooperatively enhance reaction efficiency. Stereochemical studies are consistent with an SN2-type ring-opening pathway. This methodology provides a practical complement to existing CO2-based approaches and expands the synthetic utility of Boc2O-mediated cascade chemistry.
SN - 0022-3263
SN - 1520-6904
ER -