UV light-driven asymmetric vinylogous aldol reaction of isatins with 2-alkylbenzophenones and enantioselective synthesis of 3-hydroxyoxindoles

文献情報

出版日 2021-12-07

DOI 10.1039/D1QO01555A

インパクトファクター 5.281

著者

Shixuan Cao, Jiatian Li, Taishan Yan, Jie Han

原文を見る

要旨

Chiral 3-hydroxyoxindoles are biologically important molecular motifs which are frequently present in natural products and artificial compounds. Herein, we report an ultraviolet light-driven asymmetric vinylogous aldol reaction between versatile isatins and 2-alkylbenzophenones. Under mild conditions, this reaction is catalysed by a chiral amine-derived thiourea, producing chiral 3-hydroxyoxindoles with up to 95% yields and up to 96 : 4 er enantioselectivities with a good substrate scope. Thus, it provides a new and facile method to prepare chiral 3-hydroxyoxindoles. A plausible mechanism is also proposed to rationalize product formation and enantioselectivity.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

UV light-driven asymmetric vinylogous aldol reaction of isatins with 2-alkylbenzophenones and enantioselective synthesis of 3-hydroxyoxindoles

文献情報

おすすめジャーナル

関連文献

Use of ionic liquids (ILs) for the IL-anion size-dependent formation of Cr, Mo and W nanoparticles from metal carbonyl M(CO)6 precursors

Single molecule conformational analysis of the biologically relevant DNA G-quadruplex in the promoter of the proto-oncogene c-MYC

Size matters—strong binding of the terephthalate dianion by thiourea functionalised fused [n]polynorbornane hosts

Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold

A dinuclear ruthenium(ii) complex that functions as a label-free colorimetric sensor for DNA

A simple method for the containment and purification of filled open-ended single wall carbon nanotubes using C60 molecules

Synthesis of iron oxide nanoparticles in a microfluidic device: preliminary results in a coaxial flow millichannel

Self-assembly of a peptide rod–coil: a polyproline rod and a cell-penetrating peptide Tat coil

Remote substituent effects on the photooxygenation of 9,10-diarylanthracenes: strong evidence for polar intermediates

Rapid formation of metal–organic nano-capsules gives new insight into the self-assembly process‡

こちらもおすすめ

3-イチチルビフェニルはどのように合成されますか？

8-溴-5-三氟甲基喹啉はどのように合成されますか？

ジメチル4-(4,4,5,5-テトラメチル-1,3,2-ドioxaborolan-2-基)-2,6-ピリジンジカルボイル酸フェニルアミニドの代替品はありますか？

N-(3,5-ヘキサクロロ-4-ピリドインイル)-8-メチオキシ-5-キノリンカーボン酸の市場動向や研究トレンドはどのようなものでしょうか？

イソステアロイルグリセリルは安全ですか？

1-(二苯甲基)-3,3-二氟-氮杂环丁烷の市場動向や研究トレンドはどうですか？

3-チオフェンスチオールの物理化学的性質は何ですか？

2-Methyl-2-propanyl (2S)-2-(aminomethyl)-1-piperidinecarboxylateは安全ですか？

CAS番号1316822-90-8の化合物は安全ですか？

Tert-butyl 2-(2-羟基乙基)哌嗪-1-羧酸はどのように保存すればよいですか？

掲載誌

Organic Chemistry Frontiers

おすすめ化合物

1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone

1-Isobutyl-7-methoxy-2,3,4,9-tetrahydro-1H-beta-carboline

N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-2-(2-propyn-1-yloxy)acetamide

4-azidosalicylic acid N-hydroxysuccinimide ester

8-Bromo-7-fluoro-2-methoxyquinoline

おすすめサプライヤー