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Palladium-Catalyzed Cascade Wacker/Allylation Sequence with Allylic Alcohols Leading to Allylated Dihydropyrones.


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.

SUBMITTER: Huang WY 

PROVIDER: S-EPMC6640993 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Cascade Wacker/Allylation Sequence with Allylic Alcohols Leading to Allylated Dihydropyrones.

Huang Wen-Yu WY   Nishikawa Toshio T   Nakazaki Atsuo A  

ACS omega 20170210 2


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 formylethy  ...[more]

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