Organocatalytic enantioselective construction of isatin-derived N-alkoxycarbonyl 1,3-aminonaphthols via sterically encumbered hydrocarbon-substituted quinine-based squaramide

Karahan, Seda; Tanyeli, Cihangir

doi:10.1039/c7nj01395g

Cited by 35 publications

(55 citation statements)

References 38 publications

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“…Tanyeli and colleagues recently reported an efficient synthesis of a 1,4-naphthoxazepine derivative 77 using the reaction between enantioenriched 1,3-aminonaphthol 76 and diphenylvinylsulfonium salt 1 , generated in situ from its precursor (2-bromoethyl)diphenylsulfonium triflate 3 in the presence of inorganic base under mild conditions, without any loss in enantiopurity ( Scheme 23 ) [ 48 ]. Naphthoxazepines and their derivatives have very high medicinal importance for the central nervous system as antipsychotics, antidepressants, and enzyme inhibitors.…”

Section: Reactions Of Vinylsulfonium Saltsmentioning

confidence: 99%

Recent Developments in Vinylsulfonium and Vinylsulfoxonium Salt Chemistry

2018

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This review describes advances in the literature since 2000 in the area of reactions of vinylsulfonium and vinylsulfoxonium salts, with a particular emphasis on stereoselective examples. Although the chemistry of vinylsulfonium salts was first explored back in the 1950s, and that of vinylsulfoxonium salts in the early 1970s, there has been renewed interest in these compounds since the turn of the century. This has been largely due to an increased appreciation for the many synthetic possibilities associated with these valuable electrophiles. The development of improved routes to vinylsulfonium salts allowing for their in situ generation has played a part in accelerating their study. In general, reactions of the two sulfur salt classes follow a similar mechanistic pathway: initial conjugate addition of a nucleophile to the β-position, followed by protonation of an ylide intermediate, and cyclization of tethered anion to afford monocyclic or bicyclic product (e.g. cyclopropane, aziridine, oxazole, oxazolidinone, γ-lactam or γ-lactone). Alternatively, reactions involve formation of a ylide intermediate followed by intramolecular Johnson-Corey-Chaykovsky reaction (epoxidation or cyclopropanation), and subsequent cyclization to afford the desired bicyclic product (e.g. fused bicyclic epoxide or cyclopropane).

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Section: Reactions Of Vinylsulfonium Saltsmentioning

confidence: 99%

Recent Developments in Vinylsulfonium and Vinylsulfoxonium Salt Chemistry

2018

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“…97 Aza-Friedel-Cras reaction of N-alkoxycarbonyl isatin ketimines with naphthols using a new 2-adamantyl-substituted quinine-derived squaramide catalyst (2 mol%) and 25 mg 4Å molecular sieve in CH 2 Cl 2 at À20 C for 12-48 h afforded chiral tetrasubstituted 3-amino-2-oxindoles 131 and 132 with excellent enantioselectivity up to greater than 99% ee and in 61-99% yields (Scheme 89). 98 Nano-SiO 2 -H 3 BO 3 was introduced as an environmentally benign and recyclable heterogeneous catalyst for the synthesis of aminonaphthols 133 at 40 C under solvent-free conditions aer 30-45 min in 88-95% yields without an additional cocatalyst or additive in air by Teimuri-Mofrad et al 99 (Scheme 90).…”

Section: Synthesis and Synthetic Applications Of Betti Base Derivativesmentioning

confidence: 99%

Recent advances in the synthesis and synthetic applications of Betti base (aminoalkylnaphthol) and bis-Betti base derivatives

Olyaei

Sadeghpour

2019

RSC Adv.

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“…The quinine-derived 2-adamantyl substituted squaramide 32 b was investigated in the asymmetric organocatalytic transformation for the first time. [71] It was found that this reaction is compatible with a variety of substituents on N-alkoxycarbonyl ketimines derived from isatins. Chiral isatin-derived N-alkoxycarbonyl 1,3-aminonaphthols were obtained with excellent enantioselectivity (up to > 99% ee) and in high yields (up to 99%) with 2 mol% catalyst loading (Scheme 57).…”

Section: Squaramide Derivativesmentioning

confidence: 92%

“…The quinine‐derived 2‐adamantyl substituted squaramide 32 b was investigated in the asymmetric organocatalytic transformation for the first time . It was found that this reaction is compatible with a variety of substituents on N ‐alkoxycarbonyl ketimines derived from isatins.…”

Section: Chiral Catalystsmentioning

confidence: 99%

Direct Asymmetric Arylation of Imines

et al. 2020

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The Friedel-Crafts reaction represents one of the most efficient tools for the formation of carbon-carbon bonds and direct derivatization of aromatic compounds. Asymmetric arylation of imines involving Friedel-Crafts reaction has received much interest recently. The present review summarizes the works on the asymmetric arylation of imines by different approaches including Friedel-Crafts reaction and their development to date. The review is divided into three main sections: addition reaction of arenes to imines in the presence of chiral catalysts; addition reaction of arenes to imines containing chiral tails and asymmetric coupling reaction of aryl boronic acids and imines. 4.2. Palladium Catalysts with Chiral Ligands 4.3. Nickel Catalysts with Chiral Ligands 5. Conclusions

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Organocatalytic enantioselective construction of isatin-derived N-alkoxycarbonyl 1,3-aminonaphthols via sterically encumbered hydrocarbon-substituted quinine-based squaramide

Abstract: 2-Adamantyl substituted quinine-squaramide catalyzed aza-Friedel–Crafts reaction of N-carbamate isatin ketimines with naphthol afforded chiral isatin-derived 1,3-aminonaphthols with excellent enantioselectivity up to greater than 99% and quantitative yield.

Cited by 35 publications

References 38 publications

Recent Developments in Vinylsulfonium and Vinylsulfoxonium Salt Chemistry

Recent Developments in Vinylsulfonium and Vinylsulfoxonium Salt Chemistry

Recent advances in the synthesis and synthetic applications of Betti base (aminoalkylnaphthol) and bis-Betti base derivatives

Direct Asymmetric Arylation of Imines

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