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Ruthenium-Catalyzed Tandem Cross-Metathesis/Wittig Olefination: Generation of Conjugated Dienoic Esters from Terminal Olefins

Ryan P. Murelli and Marc L. Snapper*

*Merkert Chemistry Center, Boston College, 2609 Beacon Street, Chestnut Hill, Massachusetts 02467-3860, Email: marc.snapperbc.edu

R. P. Murelli, M. L. Snapper, Org. Lett., 2007, 9, 1749-1752.

DOI: 10.1021/ol070445t (free Supporting Information)


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Abstract

In the presence of ruthenium-based olefin metathesis catalysts and triphenylphosphine, α,β-unsaturated aldehydes can be olefinated with diazoacetates. A tandem transformation of terminal olefins to 1,3-dienoic olefins in a single operation based on olefin cross-metathesis and Wittig olefination has been developed.

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Key Words

Cross-Metathesis, Wittig Reaction, 1,3-Dienes, Unsaturated Esters


ID: J54-Y2007-1300