Atroposelective Phosphoric Acid Catalyzed Three‐Component Cascade Reaction: Enantioselective Synthesis of Axially Chiral N‐Arylindoles

Lin, Xufeng; Wang, Lei; Zhong, Jialing

doi:10.1002/ange.201909855

Cited by 37 publications

(10 citation statements)

References 82 publications

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“…[20][21][22] In 2019, Lin and co-workers performedt he de novo construction of the indole ring via an asymmetric three-component cascade reaction between 2,3-diketoesters 12, ortho-substituted aryl amines 13 and 1,3-cyclohexanediones 14 in the presence of CPA( R)- C1,w hich was developed by their group, thus accomplishing the atroposelective synthesis of axially chiral N-arylindoles 15 in high yields with excellent enantioselectivities (Scheme 4a). [23] The researchers also suggested ap ossible reactionp athway of this CPA-catalyzed cascade reaction( Scheme4b).…”

Section: Catalytic Asymmetric Construction Of Axially Chiral Indole-bmentioning

confidence: 99%

Catalytic Asymmetric Construction of Axially Chiral Indole‐Based Frameworks: An Emerging Area

Liu

Tan

et al. 2020

Chemistry A European J

241

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Axially chiral indole-based frameworks have been recognized as ac lass of important five-membered heterobiaryls andd eveloping catalytic asymmetric approaches for constructingt hese frameworks in an enantioselective manner is highly desirable. In recent years, syntheticc hemists have paid much attention to this research field, and rapid developments have occurred. At this point, ar ange of axially chiral indole-based scaffolds have been constructed via various catalytic asymmetric reactions based on different strategies. Thus, the catalytic asymmetric construction of axially chiral indole-based frameworks has becomea ne merging area. This minireview summarizes the rapid advances in this field and gives some insights into future developments, which will help this research field to thrive.

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Section: Catalytic Asymmetric Construction Of Axially Chiral Indole-bmentioning

confidence: 99%

Catalytic Asymmetric Construction of Axially Chiral Indole‐Based Frameworks: An Emerging Area

Liu

Tan

et al. 2020

Chemistry A European J

241

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“…Soon after, Lin and co‐workers documented a catalytic enantioselective version of Doyle indole synthesis enable by the newly second‐generation of chiral spirocyclic phosphoric acid based on tetramethyl‐1,1’‐spirobiindane developed by their group [30] . This atroposelective three‐components tandem reaction of 2,3‐diketoesters 76 , aromatic amines 23 and 1,3‐cyclohexanediones 77 provided an efficient method for assembling highly enantioenriched axially chiral N ‐arylindoles 78 .…”

Section: Construction Of Indole‐containing Atropisomersmentioning

confidence: 99%

Chiral Phosphoric Acid: A Powerful Organocatalyst for the Asymmetric Synthesis of Heterocycles with Chiral Atropisomerism

Shao

Cheng

2020

ChemCatChem

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The past two decades have witnessed unprecedented development and advancement of chiral phosphoric acid catalysis. Therefore, it is not surprising that the attempts to synthesize enantioenriched axially chiral compounds via chiral phosphoric acid catalysis have achieved fruitful results in recent years although this area of research is still in its infancy. A number of structurally important heterocycles with chiral atropisomerism have been successfully designed and prepared by chiral phosphoric acid promoted transformations involving diverse strategies: including direct coupling, de novo formation of a heterocyclic ring and functionalization of prochiral or racemic substrates. In this minireview, we would like to highlight the advances in the field of atropisomeric heterocycles construction enabled by chiral phosphoric acid catalysis. In addition, this Minireview is organized based on the different types of atropisomeric heterocyclic frameworks generated covering quinoline, pyrrole, indole, benzimidazole, quinazolinone, isoindolinone, urazole, pyrazole and so on. We hope that this Minireview will motivate continuous interest on chiral phosphoric acid catalyzed atroposelective reactions.

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“…Through many research and exploration, the intermediate transition states of chiral phosphoric acid catalysts can be roughly divided into two categories, One is bifunctional activation ( Figure 2), and the other is Ion-pairing activation ( Figure 3) [9][10].With the development of SPA, many important asymmetric catalytic reactions such as Pictet-Spengler reaction, Fisher indolization, Diels-alder reaction and Ugi reaction have been realized [11][12][13][14].In 2019, Lin Xufeng's group obtained the first chiral phosphoric acid catalyzed axial chiral N-arylindole by using the second generation SPA catalyst. [15] A series of axially chiral arylindoles (up to 99% ee) were obtained in high yield (up to 93%) (scheme 2). The realization of these reactions not only provides a new idea for the synthesis of a variety of natural products or bioactive chiral molecules, but also expands a new space for the development and application of SPA catalysts.…”

Section: Introductionmentioning

confidence: 99%

Applications of chiral spirocyclic phosphoric acid in the synthesis of natural products

Yang

2021

E3S Web Conf.

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With a 10 years development, chiral spirocyclic phosphoric acids (SPAs) have attracted a substantial amount of attention from the synthetic organic chemistry community. This kind of small molecule organic catalysts has some advantages like easy to obtain, no transition metal and wide application range. Because of avoiding the use of toxic substances which are limited in the process of drug synthesis, a large number of studies pay attention to the key structures (such as indole, carbozole.) containing pharmacological active components in natural products. And most of them get a excellent result in yields (more than 80% yield) and enantioselectivities (more than 90% ee). These studies can provide new pathways to nature products.

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Atroposelective Phosphoric Acid Catalyzed Three‐Component Cascade Reaction: Enantioselective Synthesis of Axially Chiral N‐Arylindoles

Cited by 37 publications

References 82 publications

Catalytic Asymmetric Construction of Axially Chiral Indole‐Based Frameworks: An Emerging Area

Catalytic Asymmetric Construction of Axially Chiral Indole‐Based Frameworks: An Emerging Area

Chiral Phosphoric Acid: A Powerful Organocatalyst for the Asymmetric Synthesis of Heterocycles with Chiral Atropisomerism

Applications of chiral spirocyclic phosphoric acid in the synthesis of natural products

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