Catalytic Enone Cycloallylation via Concomitant Activation of Latent Nucleophilic and Electrophilic Partners:  Merging Organic and Transition Metal Catalysis

Upon exposure of mono-enone mono-allylic carbonates to tributylphosphine and 1 mol % Pd(Ph3P)4, efficient conversion to the corresponding cycloallylated products is achieved. This transformation combines the nucleophilic features of the Morita−Baylis−Hillman reaction with the electrophilic features...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2003-07, Vol.125 (26), p.7758-7759
Main Authors: Jellerichs, Bradley G, Kong, Jong-Rock, Krische, Michael J
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Allyl Compounds - chemical synthesis
Allyl Compounds - chemistry
Catalysis
Chemistry
Cyclization
Exact sciences and technology
Hydrocarbons, Cyclic - chemical synthesis
Ketones - chemistry
Kinetics and mechanisms
Organic chemistry
Organometallic Compounds - chemistry
Palladium - chemistry
Phosphines - chemistry
Reactivity and mechanisms
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Summary:Upon exposure of mono-enone mono-allylic carbonates to tributylphosphine and 1 mol % Pd(Ph3P)4, efficient conversion to the corresponding cycloallylated products is achieved. This transformation combines the nucleophilic features of the Morita−Baylis−Hillman reaction with the electrophilic features of the Trost−Tsuji reaction.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0301469