Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel-Crafts/Lactonization Reaction

被引：30

作者：

Ren, Hai ^{[1
]}

Wang, Pan ^{[1
]}

Wang, Lijia ^{[1
]}

Tang, Yong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 19期

关键词：

POSITIVE ALLOSTERIC MODULATOR; ENANTIOSELECTIVE ALPHA-ARYLATION; CRAFTS ALKYLATION; GABA(B) RECEPTOR; ETHYL TRIFLUOROPYRUVATE; BIS(OXAZOLINE) LIGANDS; ENE REACTION; RAC-BHFF; UPDATE; INDOLES;

D O I：

10.1021/acs.orglett.5b02440

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly enantioselective and regioselective chiral Lewis acid catalyzed tandem Friedel-Crafts/lactonization reaction is reported, providing direct access to plenty of 3-hydroxy-3-trifluoromethyl benzofuran-2-ones in up to 94% yields with up to >99% ee. Mechanistic study reveals that the interactions between the phenolic hydroxyl group and trifluoropyruvate are the most likely contributing factor to the high enantio- and regioselectivity. Optically pure (-)-BHFF can be obtained in gram-scale with 0.05 mol % catalyst, demonstrating the potentially utility of this method in medicinal chemistry.

引用

收藏

页码：4886 / 4889

页数：4

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