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Letter

Preparation and Use of Enantioenriched Allenylsilanes for the Stereoselective Synthesis of Homopropargylic Ethers

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Ryan A. Brawn and James S. Panek*

Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215

Org. Lett., 2007, 9 (14), pp 2689–2692

DOI: 10.1021/ol070936d

Publication Date (Web): June 9, 2007

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

, panek@bu.edu

Abstract

A convenient procedure for the synthesis of highly enantioenriched allenylsilanes by Johnson orthoester Claisen rearrangement of 1-silyl propargylic alcohols is described. Allenylsilanes are then used as carbon nucleophiles in three-component, Lewis acid mediated additions to in situ generated oxonium ions, resulting in enantioenriched homopropargylic ethers.

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Published In Issue July 05, 2007
Received April 20, 2007

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Letter

Preparation and Use of Enantioenriched Allenylsilanes for the Stereoselective Synthesis of Homopropargylic Ethers

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Annulations of Enantioenriched Allenylsilanes with in Situ Generated Iminium Ions: Stereoselective Synthesis of Diverse Heterocycles

Enantioselective Intramolecular Friedel−Crafts-Type α-Arylation of Aldehydes

Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton

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