Peer-reviewedCC BYThe Journal of organic chemistry
Unexpected Rearrangement of Unsaturated Lactones to Give Tricyclic Furopyrrolidinones.
- 1Department of Chemistry, University of Iowa, Iowa City, Iowa52242, United States.
Abstract
An unexpected cyanide-mediated rearrangement of conjugated lactones is described, providing access to novel tricyclic furopyrrolidinones. This reaction occurs in a stoichiometry- and substrate-dependent manner, induced by multiple additions of cyanide to α,β,γ,δ-unsaturated lactones bearing suitable aryl substituents, providing products with adjacent ether, nitrile, and lactam functionalities. Single-crystal X-ray diffraction (SCXRD) studies of two products support the stereochemical assignments, providing evidence of a dynamic equilibrium process.
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BibTeX
@article{onyeyilim2026unexpected,
title = {{Unexpected Rearrangement of Unsaturated Lactones to Give Tricyclic Furopyrrolidinones.}},
author = {Ebuka L Onyeyilim and David B C Martin},
journal = {The Journal of organic chemistry},
year = {2026},
month = oct,
doi = {10.1021/acs.joc.6c01880},
url = {https://europepmc.org/article/MED/42917576},
note = {CC BY},
}
RIS
TY - JOUR
TI - Unexpected Rearrangement of Unsaturated Lactones to Give Tricyclic Furopyrrolidinones.
AU - Ebuka L Onyeyilim
AU - David B C Martin
PY - 2026
DA - 2026/10/01
JO - The Journal of organic chemistry
DO - 10.1021/acs.joc.6c01880
UR - https://europepmc.org/article/MED/42917576
AB - An unexpected cyanide-mediated rearrangement of conjugated lactones is described, providing access to novel tricyclic furopyrrolidinones. This reaction occurs in a stoichiometry- and substrate-dependent manner, induced by multiple additions of cyanide to α,β,γ,δ-unsaturated lactones bearing suitable aryl substituents, providing products with adjacent ether, nitrile, and lactam functionalities. Single-crystal X-ray diffraction (SCXRD) studies of two products support the stereochemical assignments, providing evidence of a dynamic equilibrium process.
SN - 0022-3263
SN - 1520-6904
ER -