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Novel Synthesis of Conjugated Dienes Attached to a Quaternary Carbon Center via Pd(0)-Catalyzed Deconjugative Allylation of Alkenylidenemalonates

2003; American Chemical Society; Volume: 68; Issue: 25 Linguagem: Inglês

10.1021/jo0353334

1520-6904

Yoshihiro Sato, Yoshihiro Oonishi, Miwako Mori,

Catalytic Cross-Coupling Reactions

Palladium(0)-catalyzed deconjugative allylation of alkenylidenemalonates and alkylidenemalonates was achieved for the first time. Reactions of dimethyl 2-((E)-but-2-enylidene)malonate with various allylic acetates using LHMDS as a base in DMF in the presence of Pd(2)dba(3) (2.5 mol %) and PPh(3) (10 mol %) proceeded at room temperature to give the corresponding alpha-allylation products in good yields in a regio- and stereoselective manner. This reaction can also be used for allylation of dimethyl ethylidenemalonate or dimethyl 2-((E)-pent-2-enylidene)malonate and give the desired alpha-allylation products in good yields.