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

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 Pd2dba3 (2.5 mol %) and PPh3 (10 mol %...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-12, Vol.68 (25), p.9858-9860
Main Authors: Sato, Yoshihiro, Oonishi, Yoshihiro, Mori, Miwako
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary: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 Pd2dba3 (2.5 mol %) and PPh3 (10 mol %) proceeded at room temperature to give the corresponding α-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 α-allylation products in good yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0353334