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| - Lewis Acid-Activated Chiral Leaving Group: EnantioselectiveElectrophilic Addition to Prochiral Olefins
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| Abstract
| - A new strategy using a BINOL derivative as a chiral leaving group and Lewis acid has beendeveloped for enantioselective alkylation of prochiral olefins. (R)-2,2‘-Bis[2-(trimethylsilyl)ethoxymethyl]-1,1‘-binaphthol is demonstrated to be an effective reagent for enantioselective hydroxymethylation of silyl enol ethers and trisubstituted alkenes. Electrophilic addition to prochiral olefinsis accompanied by cleavage of an acetal that is dual activated by SnCl4 and the δ-effect of siliconthrough the SN2 substitution process. Enantioselective synthesis of cyclic terpenes is also describedusing this strategy.
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