Answers are grounded in this paper and cite their sources.
We report the diastereoselective addition of a variety of nucleophiles to alpha-(trimethylsilyl)benzyl-substituted oxocarbenium ions. The oxocarbenium ions are generated from alpha-acetoxy ethers, which are easily prepared via reductive acetylation of esters. The alpha-(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. [reaction: see text]
No takes yet. Share an insight, caveat, or question.
Rychnovsky et al. (2003) studied this question.
Synapse has enriched 10 related papers. Consider them for comparative context: