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Asymmetric Claisen Rearrangements Enabled by Catalytic Asymmetric Di(allyl) Ether Synthesis

Scott G. Nelson* and Kan Wang

*Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, Email: sgnelsonpitt.edu

S. G. Nelson, K. Wang, J. Am. Chem. Soc., 2006, 128, 4232-4233.

DOI: 10.1021/ja058172p (free Supporting Information)


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Abstract

Catalytic asymmetric synthesis of di(allyl) ethers followed by an olefin isomerization-Claisen rearrangement (ICR) reaction provides a convenient, two-step route to asymmetric aliphatic Claisen rearrangements from easily obtained starting materials.

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Stereoselective Olefin Isomerization Leading to Asymmetric Quaternary Carbon Construction

K. Wang, C. J. Bungard, S. G. Nelson, Org. Lett., 2007, 9, 2325-2328.

Catalyzed Olefin Isomerization Leading to Highly Stereoselective Claisen Rearrangements of Aliphatic Allyl Vinyl Ethers

S. G. Nelson, C. J. Bungard, K. Wang, J. Am. Chem. Soc., 2003, 125, 13000-13001.

DOI: 10.1021/ja037655v


Key Words

Addition, Tsuji-Trost Reaction, Claisen rearrangement, Aldehydes


ID: J48-Y2006-1790