Enantioselective Synthesis of Chiral 2,2-Difluoro-spiroindanone-dihydroquinazolinones by CPA-Catalyzed Cyclization Reactions

被引：1

作者：

Wei, Xing-Pin ^{[1
]}

Gao, Fen ^{[1
]}

Li, Dan ^{[1
]}

He, Yonghui ^{[2
]}

Li, Ganpeng ^{[2
]}

Zhao, Xiao-Jing ^{[3
]}

机构：

[1] Yunnan Minzu Univ, Sch Ethn Med, Kunming 650500, Peoples R China

[2] Yunnan Minzu Univ, Sch Ethn Med, Key Lab Chem Ethn Med Resources, Kunming 650500, Peoples R China

[3] Yunnan Minzu Univ, Sch Ethn Med, Key Lab Chem Ethn Med Resources, Kunming 650500, Peoples R China

来源：

ORGANIC LETTERS | 2025年 / 27卷 / 05期

基金：

中国国家自然科学基金;

关键词：

BRONSTED ACID CATALYSIS; INTRAMOLECULAR AMIDATION; ASYMMETRIC-SYNTHESIS; DIHYDROQUINAZOLINONES; TRIFLUOROMETHYLATION; FLUORINE; CYTOTOXICITY; DERIVATIVES; RECEPTOR;

D O I：

10.1021/acs.orglett.5c00043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of chiral gem-difluorinated spiro-heterocyclic compounds continues to be a significant challenge in organic chemistry due to their widespread applications across various fields. Therefore, efficient asymmetric approaches for the synthesis of gem-difluorinated spiroindanone-dihydroquinazolinones are particularly valuable, especially in the industrial manufacturing of chiral fluorinated drugs. Herein, we developed the CPA-catalyzed asymmetric enantioselective cyclization reactions of gem-difluoroalkyl 1,3-indandiones with anthranilamides to achieve various chiral 2,2-difluoro-spiroindanone-dihydroquinazolinones in good to high yields with excellent enantioselectivities. Moreover, the mechanism experiment proved that the gem-difluoro substitution pattern promotes the reaction.

引用

页码：1304 / 1309

页数：6

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