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
收藏
页码：1304 / 1309
页数：6
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