Enantioselective Catalytic Synthesis of α‐Stereogenic Chromen‐4‐one Amino Derivatives

Kovalevsky, Ruslan A.; Vasechkin, Konstantin V.; Kucherenko, Alexander S.; Zlotin, Sergei G.

doi:10.1002/adsc.202300659

Cited by 2 publications

(1 citation statement)

References 34 publications

(19 reference statements)

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“…Benzyl carbamate (1) was chosen herein as a new substrate for the study. This compound is similar in structure to benzylamine and is capable of yielding imines [105]. We failed to find information on the condensation between carbamic acid esters and glyoxal.…”

Section: Resultsmentioning

confidence: 93%

Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Paromov

2023

Molecules

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The synthesis of substituted 2,4,6,8,10,12-hexaazaisowurtzitane via direct condensation is challenging. The selection of starting ammonia derivatives is very limited. The important step in developing alternative synthetic routes to these compounds is to investigate their formation process in detail. Here, we examined an acid-catalyzed condensation between benzyl carbamate and glyoxal in a ratio of 2:1 in a range of polar protic and aprotic solvents, and discovered a new process occurring during the cascade condensation of glyoxal with ammonia derivatives as well as discovered several processes hindering the formation of caged compounds. More specifically, a cyclic compound, N,N′-bis(carbobenzoxy)-3,6-diamino-1,4-dioxane-2,5-diol, was found to form at the early stage of condensation under low acidity conditions. The formation of this compound is governed by an easier condensation of alcohol groups compared to the amide ones. The condensation intermediates, N,N′-bis(carbobenzoxy)ethan-1,2-diol, N,N′,N″-tris(carbobenzoxy)ethanol, and N,N′,N″,N‴-tetrakis(carbobenzoxy)ethan, were obtained at a higher acidity. A range of solvents were identified: those that react with benzyl carbamate, those that promote the progress of side processes, and those that promote precipitation of condensation intermediates. A few byproducts were isolated and identified. It was found that DMSO exhibits a strong deactivating ability, while CH3CN exhibits a strong activating ability towards the acid-catalyzed condensation process of benzyl carbamate with glyoxal.

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Section: Resultsmentioning

confidence: 93%

Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Paromov

2023

Molecules

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Bifunctional Squaramide‐Catalyzed Asymmetric Michael/Cyclization Reactions of 3‐Hydroxychromenones with Isatylidenemalononitriles

Geng,

2024

ChemistrySelect

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A squaramide‐catalyzed asymmetric Michael/cyclization tandem reaction between 3‐hydroxychromenones and isatylidenemalononitriles was developed. Using this strategy, a wide scope of spiro[indoline‐3,4′‐pyrano[3,2‐b]chromene] derivatives, which combined chromone, pyran, indolone in one molecule, could be obtained in moderate to excellent yields (up to 94 %) with moderate enantioselectivities (up to 95 % ee). In addition, the scaled‐up experiment also confirmed the synthetic practicality of this synthetic strategy.

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Enantioselective Catalytic Synthesis of α‐Stereogenic Chromen‐4‐one Amino Derivatives

Cited by 2 publications

References 34 publications

Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Bifunctional Squaramide‐Catalyzed Asymmetric Michael/Cyclization Reactions of 3‐Hydroxychromenones with Isatylidenemalononitriles

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