Lewis acid-activated chiral leaving group: enantioselective electrophilic addition to prochiral olefins
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Updated: Aug 16, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Hiroko Nakamura1, Kazuaki Ishihara, Hisashi Yamamoto
1Graduate School of Engineering, Nagoya University, SORST, Japan Science and Technology Corporation (JST), Chikusa, Nagoya 464-8603, Japan.
Abstract:
A new strategy using a BINOL derivative as a chiral leaving group and Lewis acid has been developed 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 olefins is accompanied by cleavage of an acetal that is dual activated by SnCl4 and the delta-effect of silicon through the S(N)2 substitution process. Enantioselective synthesis of cyclic terpenes is also described using this strategy.
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