Asymmetric synthesis of bicyclic pyran scaffolds bearing two oxa-quaternary stereocenters via zinc-catalyzed [5+1] annulations

被引：7

作者：

Zhang, Cui ^{[1
,2
]}

Jiang, Tao ^{[1
,2
]}

Hua, Yuan-Zhao ^{[1
,2
]}

Mei, Guang-Jian ^{[1
,2
]}

Wang, Min-Can ^{[1
,2
]}

Jia, Shi-Kun ^{[1
,2
]}

机构：

[1] Zhengzhou Univ, Coll Chem, Zhengzhou 450000, Henan, Peoples R China

[2] Zhengzhou Univ, Inst Green Catalysis, Zhengzhou 450000, Henan, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 18期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

MANNICH-TYPE REACTION; DIRECT SYN-ALDOL; ENANTIOSELECTIVE SYNTHESIS; GAMMA-BUTYROLACTONES; ZN CATALYSIS; TRANSFORMATIONS; HYDROXYKETONES; CONSTRUCTION; DERIVATIVES; DESIGN;

D O I：

10.1039/d3qo00925d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective [5 + 1] annulation of & alpha;-hydroxyl aryl ketones with cyclohexadienone-tethered enones via chiral dinuclear zinc catalysts is reported. A Bronsted base and Lewis acid cooperative activation model is the critical factor for the chirality transfer process, giving access to a wide array of enantioenriched bicyclic pyrans scaffolds bearing two oxa-quaternary carbon centers with good yields and high optical purities. Notably, this reaction offers a new reaction mode of & alpha;-hydroxyl ketones as C,C-bisnucleophiles in catalytic asymmetric transformation.

引用

页码：4516 / 4521

页数：7

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