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

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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Veröffentlicht in:Organic letters 2015-06, Vol.17 (12), p.3182-3185
Hauptverfasser: Nokami, Toshiki, Yamane, Yu, Oshitani, Shunsuke, Kobayashi, Jun-ka, Matsui, Shin-ichiro, Nishihara, Takashi, Uno, Hidemitsu, Hayase, Shuichi, Itoh, Toshiyuki
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Sprache:eng
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Zusammenfassung: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