Catalytic Kinetic Resolution of Spiro-Epoxyoxindoles with 1-Naphthols: Switchable Asymmetric Tandem Dearomatization/Oxa-Michael Reaction and Friedel-Crafts Alkylation of 1-Naphthols at the C4 Position

被引：48

作者：

Zhu, Gongming ^{[1
]}

Li, Yiping ^{[2
]}

Bao, Guangjun ^{[2
]}

Sun, Wangsheng ^{[2
]}

Huang, Liwu ^{[1
]}

Hong, Liang ^{[1
]}

Wang, Rui ^{[2
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China

[2] Lanzhou Univ, Sch Basic Med Sci, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Gansu, Peoples R China

来源：

ACS CATALYSIS | 2018年 / 8卷 / 03期

关键词：

asymmetric catalysis; dearomatization; Friedel-Crafts alkylation; kinetic resolution; 1-naphthols; spirooxindoles; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; BRONSTED ACID; SPIROCYCLOPENTANE BIOXINDOLES; PHOSPHORIC-ACID; CONSTRUCTION; REGIOSELECTIVITY; NAPHTHOLS; PHENOL; CYCLOHEXADIENONES; DESYMMETRIZATION;

D O I：

10.1021/acscatal.7b03268

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Switching the chemo- or regioselectivity from identical starting materials under readily tunable reaction conditions represents a great challenge in medicinal and synthetic organic chemistry. Herein, we report the asymmetric dearomatization/oxa-Michael reaction and Friedel Crafts alkylation of 1-naphthols at the C4 position, wherein the chemoselectivity could be switched easily by using different reaction conditions without changing the catalyst and the substrates. The reactions feature asymmetric Friedel Crafts alkylation of 1-naphthols at the C4 position and asymmetric dearomatization without using specific substrates or stepwise protocols.

引用

页码：1810 / 1816

页数：13

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