Abstract
A newly designed, bowl-shaped tris(2,6-diphenylbenzyl)silyl (TDS) group can be successfully utilized as a highly effective shield of ketone carbonyls for various nucleophilic attacks and α-deprotonation. The high shielding effect of the bowl-shaped TDS moiety toward carbonyl and even α-protons is verified by the 1H NMR study of TDS ketone 1a in CDCl3, and by its X-ray analysis. The TDS ketone 1b can be cleaved with Bu4NF/BF3·OEt2.
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