Asymmetric Organocatalytic Tandem Cyclization/Transfer Hydrogenation: A Synthetic Strategy for Enantioenriched Nitrogen Heterocycles

Shi, Feng; Tan, Wei; Zhang, Honghao; Mei, Li; Ye, Qin; Ma, Guan‐Hua; Tu, Shu‐Jiang; Li, Guigen

doi:10.1002/adsc.201300576

Cited by 53 publications

(16 citation statements)

References 43 publications

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“…An asymmetric organocatalytic tandem process comprising a cyclization reaction followed by a transfer hydrogenation has been established, leading to the step-economical synthesis of enantioenriched dihydroquinoxalinones from readily accessible materials with excellent enantio-selectivity (up to 99% ee). This strategy provided an easy access to biologically significant chiral N-heterocycles [43,44]. Catalysts bearing multiple H-bond donors have shown great potential to generate better levels of enantio-selectivity in the reactions [41].…”

Section: Supramolecular Organocatalysismentioning

confidence: 99%

“…This approach was applied in the preparation of bicyclo [3.2.1] octane (41) employing bifunctional organocatalysts (42) (thiourea and tertiary amine) [16]. The reaction worked very well for several substituted β,γ-unsaturated 1,2-ketoesters (43) and cyclic 1,3ketoesters (44). It allows for the formation of the correspondent bicyclo[3.2.1]octanes in good yields (53−98%) with enantioselectivities up to 90% ee (Scheme 9).…”

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confidence: 99%

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Organocatalysis: A Brief Overview on Its Evolution and Applications

2018

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The use of small organic molecules as catalysts has gained increasing importance recently. These substances, the so-called organocatalysts, present a lot of advantages, like being less toxic, less polluting, and more economically viable than the organometallic catalysts that dominate asymmetric synthesis. This work intends to briefly show some classic works and recent publications, explaining the advantages of organocatalysis and the different types of compounds used in this field, as well as their course of action.

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Section: Supramolecular Organocatalysismentioning

confidence: 99%

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confidence: 99%

Organocatalysis: A Brief Overview on Its Evolution and Applications

2018

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“…A chiral phosphoric acid 1 ‐catalyzed asymmetric reductive cyclization of phenylglyoxal with o ‐phenylenediamine has also been reported by using Hantzsch ester 2 as the hydride source (Scheme ). The reaction yielded ( R )‐2‐phenyl‐1,2,3,4‐tetrahydroquinoxaline 3 with excellent yield and ee value …”

Section: Aliphatic Axb3 Smentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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“…dihydroquinoxalinones 37 from readily accessible materials with excellent results in terms of reactivity and enantioselectivity (Scheme 3.13) [44]. …”

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Organocatalytic Transfer Hydrogenation and Hydrosilylation Reactions

Herrera

2016

Top Curr Chem (Z)

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The reduction of different carbon-carbon or carbon-heteroatom double bonds is a powerful tool that generates in many cases new chiral centers. In the last decade, the organocatalytic version of these transformations has attracted more attention, and remarkable progresses have been made in this way. Organocatalysts such as chiral Brønsted acids, thioureas, chiral secondary amines or Lewis bases have been successfully used for this purpose. In this context, this chapter will cover pioneering and seminal examples using Hantzsch dihydropyridines 1 and trichlorosilane 2 as reducing agents. More recent examples will be also cited in order to cover as much as possible the complete research in this field.

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Asymmetric Organocatalytic Tandem Cyclization/Transfer Hydrogenation: A Synthetic Strategy for Enantioenriched Nitrogen Heterocycles

Cited by 53 publications

References 43 publications

Organocatalysis: A Brief Overview on Its Evolution and Applications

Organocatalysis: A Brief Overview on Its Evolution and Applications

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Organocatalytic Transfer Hydrogenation and Hydrosilylation Reactions

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