Asymmetric Dearomative Fluorination of 2-Naphthols with a Dicarboxylate Phase-Transfer Catalyst

被引：51

作者：

Egami, Hiromichi ^{[1
]}

Rouno, Taiki ^{[1
]}

Niwa, Tomoki ^{[1
]}

Masuda, Kousuke ^{[1
]}

Yamashita, Kenji ^{[1
]}

Hamashima, Yoshitaka ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, 52-1 Yada, Shizuoka 4228526, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 33期

关键词：

asymmetric catalysis; dearomatization; fluorination; naphthols; phase-transfer catalysis; HYDROXYLATIVE PHENOL DEAROMATIZATION; C-H TRIFLUOROMETHYLATION; ANTIBACTERIAL ACTIVITY; ENANTIOSELECTIVE DEAROMATIZATION; OXIDATIVE DEAROMATIZATION; BETA-NAPHTHOL; LACINILENE-C; METHYL-ETHER; CONSTRUCTION; DERIVATIVES;

D O I：

10.1002/anie.202005367

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A linked dicarboxylate phase-transfer catalyst enables smooth asymmetric dearomative fluorination of 2-naphthols with Selectfluor under mild conditions to give the corresponding 1-fluoronaphthalenone derivatives in a highly enantioselective manner. This reaction, which is compatible with a range of functional groups, is the first example of catalytic asymmetric fluorination of 2-naphthols, and is expected to be useful in the synthesis of bioactive molecules.

引用

页码：14101 / 14105

页数：5

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