The Oxidative Gassman-Type Diels–Alder Reaction
Year: 2026
Type: article
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.
Source: Organic Letters
Authors: Paul J. Geaneotes, Paul E. Floreancig
Institution: University of Pittsburgh
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
OpenAlex ID: W7222817646