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Updated: Feb 6, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
2-Picoline catalyst-triggered [2 + 2 + 2] cycloaddition-type reaction of acetylenedicarboxylates, aldehydes and
Keiichiro Tateishi1, Keiichi Noguchi, Akio Saito
1Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan. akio-sai@cc.tuat.ac.jp.
Abstract:
2-Picoline efficiently catalyzes the formation of α,β-enones from acetylenedicarboxylates and aldehydes in the presence of alkenes, thereby leading to pyrans in moderate to good yields with complete regioselectivities. This synthetic method of pyrans is represented as a first example of catalytic and direct [2 + 2 + 2] cycloaddition of three different components under the metal-free conditions.
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