Organocatalytic asymmetric Friedel–Crafts alkylation/hemiketalization/lactonization cascade reactions: highly enantioselective synthesis of furo[2,3-b]benzofuranones

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成果类型：

期刊论文

作者：

Xu, Kunhua;Chen, Wenming;Chen, Xu;Wang, Biao;Huang, Jun;...

通讯作者：

Tian, X;Huang, J

作者机构：

[Xu, Kunhua; Wang, Biao; Tian, Xu; Chen, Xu] Guangzhou Med Univ, Key Lab Mol Target & Clin Pharmacol, Guangzhou 511436, Guangdong, Peoples R China.

[Xu, Kunhua; Wang, Biao; Tian, Xu; Chen, Xu] Guangzhou Med Univ, State Key Lab Resp Dis, Sch Pharmaceut Sci, Guangzhou 511436, Guangdong, Peoples R China.

[Xu, Kunhua; Wang, Biao; Tian, Xu; Chen, Xu] Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China.

[Chen, Wenming] Hunan Univ Chinese Med, Affiliated Hosp 1, Dept Pharmaceut Prod Ctr, Shaoshan Rd 95, Changsha 410007, Hunan, Peoples R China.

[Huang, Jun] Guangzhou Med Univ, Affiliated Hosp 2, Sino French Hoffmann Inst, Guangdong Prov Key Lab Allergy & Clin Immunol, Guangzhou 511436, Guangdong, Peoples R China.

通讯机构：

[Tian, X ; Huang, J ] G

Guangzhou Med Univ, Key Lab Mol Target & Clin Pharmacol, Guangzhou 511436, Guangdong, Peoples R China.

Guangzhou Med Univ, State Key Lab Resp Dis, Sch Pharmaceut Sci, Guangzhou 511436, Guangdong, Peoples R China.

Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China.

Guangzhou Med Univ, Affiliated Hosp 2, Sino French Hoffmann Inst, Guangdong Prov Key Lab Allergy & Clin Immunol, Guangzhou 511436, Guangdong, Peoples R China.

语种：

英文

关键词：

Alkylation;Amides;Functional groups;Synthesis (chemical);Amide functional group;Enantioselective synthesis;Friedel-Crafts alkylation;High stereoselectivities;Medicinal chemistry;Mild reaction conditions;Natural product synthesis;Stereogenic centers;Selective catalytic reduction

期刊：

Organic Chemistry Frontiers

ISSN：

2052-4110

年：

2020

卷：

期：

页码：

1679-1684

DOI：

10.1039/d0qo00475h

基金类别：

We are grateful for the support provided for this study by the National Science Foundation of China (21702035), GDUPS (2017), the Pearl River Talents Recruitment Program of Guangdong Province (2017GC010600), and Science and Technology Program of Guangzhou (201804010455).

机构署名：

本校为其他机构

院系归属：

第一中医临床学院

摘要：

An efficient asymmetric organocatalytic Friedel-Crafts alkylation/hemiketalization/lactonization cascade reaction of 3-ylidene oxindoles with 2-naphthols and activated phenols has been developed. In the presence of 5 mol% of a bifunctional squaramide catalyst, this scalable cascade reaction affords a series of novel furo[2,3-b]benzofuranone derivatives with three adjacent stereogenic centers in good to excellent yields (up to 91%) and with high stereoselectivities (up to 96% ee, >20 : 1 d.r.). Moreover, this cascade reaction provides a distin...

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Organocatalytic asymmetric Friedel–Crafts alkylation/hemiketalization/lactonization cascade reactions: highly enantioselective synthesis of furo[2,3-b]benzofuranones

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