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

Org Lett

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

Published: July 2007

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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http://dx.doi.org/10.1021/ol070936dDOI Listing

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