Diastereoselective Additions of Nucleophiles to α-Acetoxy Ethers Using the α-(Trimethylsilyl)benzyl Auxiliary

Diastereoselective Additions of Nucleophiles to α-Acetoxy Ethers Using the α-(Trimethylsilyl)benzyl Auxiliary

We report the diastereoselective addition of a variety of nucleophiles to α-(trimethylsilyl)benzyl-substituted oxocarbenium ions. The oxocarbenium ions are generated from α-acetoxy ethers, which are easily prepared via reductive acetylation of esters. The α-(trimethylsilyl)benzyl auxiliary produces...

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Veröffentlicht in:Organic letters 2003-06, Vol.5 (13), p.2367-2370
Hauptverfasser: Rychnovsky, Scott D, Cossrow, Jennifer
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Cossrow, Jennifer
description We report the diastereoselective addition of a variety of nucleophiles to α-(trimethylsilyl)benzyl-substituted oxocarbenium ions. The oxocarbenium ions are generated from α-acetoxy ethers, which are easily prepared via reductive acetylation of esters. The α-(trimethylsilyl)benzyl auxiliary produces good to excellent facial selectivity with a variety of nucleophiles, including silyl enol ethers, silyl ketene acetals, allylsilanes, and crotylsilanes. The utility of this auxiliary is further demonstrated in a complex ketone aldol coupling reaction.
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title Diastereoselective Additions of Nucleophiles to α-Acetoxy Ethers Using the α-(Trimethylsilyl)benzyl Auxiliary
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