Organic Letters 2007-07-05

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

Ryan A Brawn, James S Panek

Index: Org. Lett. 9 , 2689, (2007)

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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.