4.8 Article

Preparation and use of enantioenriched allenylsilanes for the stereoselective synthesis of homopropargylic ethers

Journal

ORGANIC LETTERS
Volume 9, Issue 14, Pages 2689-2692

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol070936d

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Funding

  1. NCI NIH HHS [CA 53604] Funding Source: Medline

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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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