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Updated: Aug 17, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
beta-Acyloxysulfonyl tethers for intramolecular Diels-Alder cycloaddition reactions
Nataliya Chumachenko1, Paul Sampson, Allen D Hunter
1Department of Chemistry, Kent State University, Ohio 44242, USA.
Abstract:
[reaction: see text]. beta-Hydroxy sulfone-based tethers were employed for the first time to achieve thermally mediated intramolecular Diels-Alder cycloaddition. The reactions proceeded with complete regioselectivity and high (10/1) to complete endo/exo-selectivity and resulted in the preferential formation of one of the two possible endo-cycloadducts. The yields and stereoselectivities were proportional to the bulk of the R(1) substituent on the beta-acyloxysulfonyl tether.
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