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Synfacts 2011(9): 0977-0977  
DOI: 10.1055/s-0030-1260909
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Elimination-Isomerization of Enol Triflates into 1,3-Dienes

Contributor(s): Hisashi Yamamoto, Susumu Oda
I. T. Crouch, T. Dreier, D. E. Frantz*
The University of Texas at San Antonio, USA
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

1,3-Dienes are used for a variety of transformations in organic synthesis. Despite its usefulness, the stereoselective synthesis of substituted 1,3-dienes is still challenging. In this paper, the authors describe the palladium-catalyzed elimination-isomerization of enol triflates into 1,3-dienes. They found reactivity differences between E- and Z-enolates and developed an effective catalytic system for each enolate by tuning bases and additives.