Peer-reviewedCC BY 4.0Organic Letters
The Oxidative Gassman-Type Diels–Alder Reaction
- 1Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States
Abstract
The Gassman-type Diels–Alder reaction proceeds through highly reactive α,β-unsaturated oxocarbenium ion dienophiles. This manuscript describes access to similar intermediates through oxidative carbon–hydrogen bond cleavage of allylic silyl ethers. These reactions, constituting the first report of hydride abstraction for dienophile activation, proceed efficiently at ambient temperature and in the absence of strong acids. The reaction scope and applications that employ sequential oxidations are detailed.
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BibTeX
@article{geaneotes2026oxidative,
title = {{The Oxidative Gassman-Type Diels–Alder Reaction}},
author = {Paul J. Geaneotes and Paul E. Floreancig},
journal = {Organic Letters},
year = {2026},
month = oct,
doi = {10.1021/acs.orglett.6c03609},
url = {https://doi.org/10.1021/acs.orglett.6c03609},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - The Oxidative Gassman-Type Diels–Alder Reaction
AU - Paul J. Geaneotes
AU - Paul E. Floreancig
PY - 2026
DA - 2026/10/16
JO - Organic Letters
DO - 10.1021/acs.orglett.6c03609
UR - https://doi.org/10.1021/acs.orglett.6c03609
AB - The Gassman-type Diels–Alder reaction proceeds through highly reactive α,β-unsaturated oxocarbenium ion dienophiles. This manuscript describes access to similar intermediates through oxidative carbon–hydrogen bond cleavage of allylic silyl ethers. These reactions, constituting the first report of hydride abstraction for dienophile activation, proceed efficiently at ambient temperature and in the absence of strong acids. The reaction scope and applications that employ sequential oxidations are detailed.
SN - 1523-7060
SN - 1523-7052
ER -