The β‑Silyl Effect on the Memory of Chirality in Friedel–Crafts Alkylation Using Chiral α‑Aryl Alcohols

Iron salt-catalyzed Friedel–Crafts alkylation of chiral α-aryl alcohols with a trimethylsilyl group was found to proceed with retention of the configuration of the hydroxyl group as a leaving group. The memory of chirality of this system stems from the β-silyl effect of the trimethylsilyl group on t...

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Bibliographic Details
Published in:Organic letters 2015-06, Vol.17 (12), p.3182-3185
Main Authors: Nokami, Toshiki, Yamane, Yu, Oshitani, Shunsuke, Kobayashi, Jun-ka, Matsui, Shin-ichiro, Nishihara, Takashi, Uno, Hidemitsu, Hayase, Shuichi, Itoh, Toshiyuki
Format: Article
Language:English
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Summary:Iron salt-catalyzed Friedel–Crafts alkylation of chiral α-aryl alcohols with a trimethylsilyl group was found to proceed with retention of the configuration of the hydroxyl group as a leaving group. The memory of chirality of this system stems from the β-silyl effect of the trimethylsilyl group on the carbocation intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01582