Visible-Light-Mediated Formal Carbene Insertion Reaction: Enantioselective Synthesis of 1,4-Dicarbonyl Compounds Containing All-Carbon Quaternary Stereocenter

被引：41

作者：

Zhang, Hua ^{[1
]}

Wang, Zheyuan ^{[1
]}

Wang, Zirui ^{[1
]}

Chu, Yunpeng ^{[1
]}

Wang, Shuncheng ^{[1
]}

Hui, Xin-Ping ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ACS CATALYSIS | 2022年 / 12卷 / 09期

基金：

中国国家自然科学基金;

关键词：

chiral phosphoric acid; carbene; visible light; 1,4-dicarbonyl compounds; diazoesters; INTERMOLECULAR STETTER REACTION; CHIRAL BRONSTED ACIDS; DIAZO-COMPOUNDS; C-C; FUNCTIONALIZATION; ACTIVATION; TRANSFORMATIONS; CATALYSIS; ALDEHYDES; STRATEGY;

D O I：

10.1021/acscatal.2c00064

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We developed an efficient visible-light-mediated formal carbene insertion reaction of 1,3-diketones with diazoesters for the construction of enantioenriched 1,4-dicarbonyl compounds with a quaternary carbon center. Combining visible light and a Bronsted acid catalyst, chiral 1,4-dicarbonyl compounds were achieved in good yields with high enantioselectivities by a photochemical carbene transfer protocol.

引用

页码：5510 / 5516

页数：7

共 16 条

[1] Synthesis of 1,4-Dicarbonyl Compounds by Visible-Light-Mediated Cross-Coupling Reactions of α-Chlorocarbonyls and Enol Acetates
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[2] Stereo- and enantioselective synthesis of chiral compounds bearing an all-carbon quaternary stereocenter by ZACA reaction
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[3] Visible-Light-Mediated Energy Transfer Enables Cyclopropanes Bearing Contiguous All-Carbon Quaternary Centers
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[4] Synthesis of 1,4-Dicarbonyl Compounds via Visible-Light-Induced Decarboxylative Radical Cascade Reactions
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[7] Enantioselective synthesis of bicarbocyclic structures with an all-carbon quaternary stereocenter through sequential cross metathesis and intramolecular Rauhut-Currier reaction
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[8] Visible-light-induced alkoxycarbonylation/cyclization of 1,7-enynes: synthesis of dihydropyranones containing all-carbon quaternary centers
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[9] Enantioselective Conjugate Addition of Donor-Acceptor Hydrazones to α,β-Unsaturated Aldehydes through Formal Diaza-Ene Reaction: Access to 1,4-Dicarbonyl Compounds
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[10] Enantioselective Synthesis of an All-Carbon Quaternary Stereocenter by Chiral Br?nsted Acid-Catalyzed Friedel-Crafts-Type Reaction between Pyrroles and 3-Indolylmethanols
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