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Communication

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

Supporting Info

Scott G. Nelson* and Kan Wang

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260

J. Am. Chem. Soc., 2006, 128 (13), pp 4232–4233

DOI: 10.1021/ja058172p

Publication Date (Web): March 11, 2006

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

, sgnelson@pitt.edu

Abstract

Merging the catalytic asymmetric synthesis of di(allyl) ethers with ensuing olefin isomerization-Claisen rearrangement (ICR) reactions provides a convenient, two-step route to asymmetric aliphatic Claisen rearrangements from easily obtained starting materials. These reactions deliver the 2,3-disubstituted 4-pentenal derivatives characteristic of aliphatic Claisen rearrangements with excellent relative and absolute stereocontrol. A catalytic enantioselective synthesis of the (+)-calopin dimethyl ether demonstrates the utility of this reaction technology in asymmetric synthesis enterprises.

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Published In Issue April 05, 2006
Received December 1, 2005

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Communication

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

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

Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades

Stereoselective Construction of Seven-Membered Rings with an All-Carbon Quaternary Center by Direct Tiffeneau−Demjanov-type Ring Expansion

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