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

被引：20

作者：

Nokami, Toshiki ^{[1
,2
]}

Yamane, Yu ^{[1
]}

Oshitani, Shunsuke ^{[1
]}

Kobayashi, Jun-ka ^{[1
]}

Matsui, Shin-ichiro ^{[1
]}

Nishihara, Takashi ^{[1
]}

Uno, Hidemitsu ^{[3
]}

Hayase, Shuichi ^{[1
,2
]}

Itoh, Toshiyuki ^{[1
,2
]}

机构：

[1] Tottori Univ, Dept Chem & Biotechnol, Grad Sch Engn, Tottori, Tottori 6808552, Japan

[2] Tottori Univ, Ctr Res Green Sustainable Chem, Grad Sch Engn, Tottori, Tottori 6808552, Japan

[3] Ehime Univ, Grad Sch Sci & Engn, Dept Biol & Chem, Matsuyama, Ehime 7908577, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 12期

关键词：

STEREOSELECTIVE-SYNTHESIS; INTERMOLECULAR REACTIONS; BENZYLIC CARBOCATIONS; S(N)1-TYPE REACTIONS; STYRENE DERIVATIVES; BOND FORMATION; DIASTEREOSELECTIVITY; CYCLIZATION; PYRROLE; INDOLES;

D O I：

10.1021/acs.orglett.5b01582

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iron salt-catalyzed Friedel-Crafts alkylation of chiral alpha-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 beta-silyl effect of the trimethylsilyl group on the carbocation intermediate.

引用

页码：3182 / 3185

页数：4

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