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.
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