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
Org. Lett., 2007, 9 (9), pp 1749–1752
DOI: 10.1021/ol070445t
Publication Date (Web): March 31, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, marc.snapper@bc.edu

Abstract

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In the presence of ruthenium-based olefin metathesis catalysts and triphenylphosphine, α,β-unsaturated aldehydes can be olefinated with diazoacetates. This ruthenium-catalyzed transformation has been employed in tandem with olefin cross-metathesis to convert terminal olefins into 1,3-dienoic esters in a single operation.

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History

  • Published In Issue April 26, 2007
  • Received February 21, 2007

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