Enantioselective catalytic Povarov reactions

Clerigué, José; Ramos, M. Teresa; Menéndez, J. Carlos

doi:10.1039/d1ob02270a

Cited by 27 publications

(13 citation statements)

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“…Asymmetric Povarov protocols have experienced significant growth in recent years. 100,108 Chen, Zhou, and co-workers described a CPA-catalyzed three-component Povarov reaction with subsequent DDQ oxidation to provide axially chiral quinoline-naphthalene compounds (Scheme 33). 109 The protocol started with imine formation between aniline and benzaldehyde derivatives, followed by the stereoselective (4 + 2) cycloaddition reaction with 1-styryl naphthols.…”

Section: Reviewmentioning

confidence: 99%

An update on chiral phosphoric acid organocatalyzed stereoselective reactions

Jiménez

2023

Org. Biomol. Chem.

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Section: Reviewmentioning

confidence: 99%

An update on chiral phosphoric acid organocatalyzed stereoselective reactions

Jiménez

2023

Org. Biomol. Chem.

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“…A Povarov reaction is a Diels–Alder reaction between an N -aryl imine and an electron-rich dienophile in the presence of Lewis acid as catalyst, used for the synthesis of quinolines [ 78 , 79 , 80 , 81 , 82 ]. The reaction is an inverse electron demand Diels–Alder (IEDDA).…”

Section: Synthetic Strategies For the Preparation Of Fused Pyridocoum...mentioning

confidence: 99%

An Overview on the Synthesis of Fused Pyridocoumarins with Biological Interest

Douka¹,

Litinas²

2022

Molecules

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Pyridocoumarins are a class of synthetic and naturally occurring organic compounds with interesting biological activities. This review focuses on the synthetic strategies for the synthesis of pyridocoumarins and presents the biological properties of those compounds. The synthesis involves the formation of the pyridine ring, at first, from a coumarin derivative, such as aminocoumarins, hydroxycoumarins, or other coumarins. The formation of a pyranone moiety follows from an existing pyridine or piperidine or phenol derivative. For the above syntheses, [4 + 2] cycloaddition reactions, multi-component reactions (MCR), as well as metal-catalyzed reactions, are useful. Pyridocoumarins present anti-cancer, anti-HIV, antimalarial, analgesic, antidiabetic, antibacterial, antifungal, anti-inflammatory, and antioxidant activities.

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“…4,5 Examples include the natural There are many synthetic routes to access chiral THQ, 5 but the simplest and most versatile to implement with a multicomponent approach remains the asymmetric Povarov reaction. 10,11 Synthesis of highly optically pure THQs can be achieved by enantioselective Povarov reactions based on a [4+2] cycloaddition or a Mannich/Friedel-Craft sequence mechanism. 4 The seminal work by Kobayashi and co-workers showed that trisubstituted THQ can be obtained in good enantioselectivity with a cis-2,3 and cis-3,4 configuration (Scheme 1, Eq.1).…”

Section: Introductionmentioning

confidence: 99%

“…There are many synthetic routes to access chiral THQ, [5] but the simplest and most versatile to implement with a multicomponent approach remains the asymmetric Povarov reaction [10,11] . Synthesis of highly optically pure THQs can be achieved by enantioselective Povarov reactions based on a [4+2] cycloaddition or a Mannich/Friedel‐Craft sequence mechanism [4] .…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Approach for Expanding the Three‐Dimensional Space of Tetrahydroquinoline to Develop BET Bromodomain Inhibitors**

Lespinasse

Wei

Perrin

et al. 2022

Chemistry A European J

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The pharmaceutical industry has a pervasive need for chiral specific molecules with optimal affinity for their biological targets. However, the mass production of such compounds is currently limited by conventional chemical routes, that are costly and have an environmental impact. Here, we propose an easy access to obtain new tetrahydroquinolines, a motif found in many bioactive compounds, that is rapid and cost effective. Starting from simple raw materials, the procedure uses a proline-catalyzed Mannich reaction followed by the addition of BF3.OEt2, which generates a highly electrophilic aza-ortho-quinone methide intermediate capable of reacting with different nucleophiles to form the diversely functionalized tetrahydroquinoline. Moreover, this enantioselective one-pot process provides access for the first time to tetrahydroquinolines with a cis-2,3 and trans-3,4 configuration. As proof of concept, we demonstrate that a three-step reaction sequence, from simple and inexpensive starting compounds and catalysts, can generate a BD2-selective BET bromodomain inhibitor with anti-inflammatory effect. product Helquinoline, 6 the synthetic products Torcetrapib, 7 MK-8318 8 and compound 1 9 (Figure 1). In all these bioactive products, chirality plays an important role since having the correct enantiomer is essential for bioactivity and selectivity.Scheme 1. Enantioselective Povarov reactions to give tri-substituted tetrahydroquinoline.

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Enantioselective catalytic Povarov reactions

Abstract: Catalytic asymmetric Povarov protocols have undergone an explosive growth, especially in the last ten years, since the first example was published in 1996. The use of chiral Lewis and Brønsted...

Cited by 27 publications

References 93 publications

An update on chiral phosphoric acid organocatalyzed stereoselective reactions

An update on chiral phosphoric acid organocatalyzed stereoselective reactions

An Overview on the Synthesis of Fused Pyridocoumarins with Biological Interest

Enantioselective Approach for Expanding the Three‐Dimensional Space of Tetrahydroquinoline to Develop BET Bromodomain Inhibitors**

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