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Stereocontrolled Synthesis of (E,Z)-Dienals via Tandem Rh(I)-Catalyzed Rearrangement of Propargyl Vinyl Ethers

Dinesh V. Vidhani*, Marie E. Krafft and Igor V. Alabugin*

*Department of Chemistry & Biochemistry, Florida State University, Tallahassee, Florida 32306, United States, Email: alabuginchem.fsu.edu

D. V. Vidhani, M. E. Krafft, I. V. Alabugin, Org. Lett., 2013, 15, 4462-4465.

DOI: 10.1021/ol4019985 (free Supporting Information)


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Abstract

A Rh(I)-catalyzed propargyl Claisen rearrangement followed by stereoselective hydrogen transfer enables the synthesis of functionalized (E,Z) dienals from propargyl vinyl ethers. Z-Stereochemistry of the first double bond suggests the involvement of a six-membered cyclic intermediate whereas the E-stereochemistry of the second double bond stems from the subsequent protodemetalation step giving an (E,Z)-dienal.

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Key Words

dienes, enales, Claisen Rearrangement


ID: J54-Y2013