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

• DOI: 10.1021/acs.orglett.5b01582
• Publication Date: 2015-06-12T01:16:38Z
• Authors: Toshiki Nokami; Yu Yamane; Shunsuke Oshitani; Jun-ka Kobayashi; Shin-ichiro Matsui; Takashi Nishihara; Hidemitsu Uno; Shuichi Hayase; Toshiyuki Itoh
• Keywords: Carbocation; Trimethylsilyl; Friedel–Crafts reaction; Chirality

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