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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Palladium-Catalyzed Cascade Wacker/Allylation Sequence with Allylic Alcohols Leading to Allylated Dihydropyrones
Wen-Yu Huang1, Toshio Nishikawa1, Atsuo Nakazaki1
1Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8601, Japan.
Abstract:
We describe a cascade Wacker/allylation sequence of β-hydroxy ynones by directly using simple allylic alcohols. This palladium(II)-catalyzed reaction occurs under mild conditions (0 °C to room temperature) and provides a new and efficient synthetic method for the preparation of allylated dihydropyrones. The regiochemical outcomes are consistent with a reaction pathway that includes an insertion/β-OH elimination sequence to form the allylic moiety. A remarkable changeover from allyl to formylethyl products occurs under the simple action of LiBr.
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