Palladium-Catalyzed Arylation of Ketone Enolates:  An Expeditious Entry to Tamoxifen-Related 1,2,2-Triarylethanones

After a rigorous study on the effect of several catalytic systems, a simple, high yielding procedure for the preparation of 1,2,2-triarylethanones, skeletal analogues of tamoxifen, is presented. Apart from the economic and environmental advantages involved, this palladium-catalyzed arylation of deox...

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Bibliographic Details
Published in:Organic letters 2002-05, Vol.4 (9), p.1591-1594
Main Authors: Churruca, Fátima, SanMartin, Raul, Tellitu, Imanol, Domínguez, Esther
Format: Article
Language:English
Subjects:
Alkylation
Antineoplastic Agents, Hormonal - chemical synthesis
Antineoplastic Agents, Hormonal - chemistry
Catalysis
Indicators and Reagents
Ketones - chemistry
Palladium
Tamoxifen - analogs & derivatives
Tamoxifen - chemical synthesis
Tamoxifen - chemistry
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Summary:After a rigorous study on the effect of several catalytic systems, a simple, high yielding procedure for the preparation of 1,2,2-triarylethanones, skeletal analogues of tamoxifen, is presented. Apart from the economic and environmental advantages involved, this palladium-catalyzed arylation of deoxybenzoin enolates features a lack of ortho-arylation side reactions. In addition, an alternative approach from acetophenones to the target triarylethanone system is also announced.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol025811h