Asymmetric Synthesis of Spiropyrazolone-Fused Dihydrofuran- naphthoquinones Bearing Contiguous Stereocenters via a Michael Addition/Chlorination/Nucleophilic Substitution Sequence

被引:2
|
作者
Li, Gaihui [1 ]
Zhang, Hongyu [1 ]
Zhang, Guoshun [1 ]
Wei, Bei [1 ]
Liu, Bin [1 ]
Song, Heng [1 ,3 ]
Li, Qingshan [1 ,2 ]
Ban, Shurong [1 ]
机构
[1] Shanxi Med Univ, Sch Pharm, Taiyuan 030001, Shanxi, Peoples R China
[2] Shanxi Univ Tradit Chinese Med, Shanxi Key Lab Chron Inflammatory Targeted Drugs, Jinzhong 030619, Shanxi, Peoples R China
[3] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 07期
基金
中国国家自然科学基金;
关键词
ENANTIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; UNSATURATED PYRAZOLONES; CASCADE; CONSTRUCTION; DERIVATIVES; SCAFFOLDS; INHIBITORS; OXINDOLES; THIOLS;
D O I
10.1021/acs.joc.2c03013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective synthesis of spiropyrazolone-fused dihydrofuran-naphthoquinones is first demonstrated via a Michael addition/Chlorination/Nucleophilic substitution se-quence. The reactions of 2-hydroxy-1,4-naphthoquinone and alpha,beta- unsaturated pyrazolones in the presence of the cinchona alkaloid derived hydrogen-bonding catalyst and NCS provide spiropyr-azolone-fused 2,3-dihydronaphtho[2,3-b]furan-4,9-diones bearing contiguous stereocenters, of which one is the spiro quaternary stereocenter in high yields with exclusive diastereoselectivity and good to excellent enantioselectivities.
引用
收藏
页码:4809 / 4813
页数:5
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