Synthesis of Sugar-Derived 2′- and 3′-Substituted Furans and Their Application in Diels−Alder Reactions

Jarosz, Sławomir; Mach, Mateusz; Szewczyk, Katarzyna; Skóra, Stanisław; Ciunik, Zbigniew

doi:10.1002/1099-0690(200108)2001:15<2955::aid-ejoc2955>3.0.co;2-0

Cited by 14 publications

(8 citation statements)

References 18 publications

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“…The identity of product 7a was confirmed by comparing its 1 H NMR spectrum with the reported literature. 25 Competitive DA reactions between 5 and 5b A mixture of diene 5 (226 mg, 1.0 mmol), 5b (96 mg, 1.0 mmol) and NPM (4 mg, 0.25 mmol) in toluene (5.0 mL) was heated under reflux. After about 30 min, TLC experiment showed formation of 6.…”

Section: Da Reaction With Maleic Anhydridementioning

confidence: 99%

Sequential Diels–Alder Reactions in a Conjugated Tetraene System

Abaee

Mohammadi

et al. 2016

Journal of Chemical Research

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The [4 + 2] cycloaddition of a conjugated diene with a substituted dienophile, known as the Diels-Alder (DA) reaction, 1 has emerged as one of the most practised organic reactions in education, 2,3 research 4,5 and industry 6,7 over the last several decades. Consequently, several reviews, 8,9 book chapters 10 and monographs 11 have highlighted the extensive synthetic applications of this reaction. By considering frontier molecular orbital (FMO) theory, 12 one would expect that in a "normal electron demand" DA reaction, an electron-rich diene would react more readily with an electron-poor dienophile since such a combination has a more energetically favourable HOMO-LUMO interaction. Thus, it is not surprising that furans, which inherently demonstrate reversible [4 + 2] reactions due to losing aromaticity after cycloaddition, 13,14 usually prefer to react with electron-deficient dienophiles. 15,16 In the framework of our studies on aldol condensation reactions, 17,18 we synthesised a series of styrylcyclohex-2enone dienes 19 which were explored for their DA reactivity in our laboratory. 20,21 In continuation, we now report a furanyl derivative of these dienes 1 which exhibits a double DA process with N-phenylmaleimide (NPM, 2a), where both the main cyclohex-2-en-1-one and the furanyl fragments react sequentially with 2a (Scheme 1). In this study, we have tried to conduct appropriate experiments to shed some light on this process. This work shows how the first cyclisation with 2a at the more active site converts the electron-poor furanyl component into an active diene which can then react with the remaining 2a. Thus, the complete consumption of 1 is only observed when two equivalents of 2a are used.

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Section: Da Reaction With Maleic Anhydridementioning

confidence: 99%

Sequential Diels–Alder Reactions in a Conjugated Tetraene System

Abaee

Mohammadi

et al. 2016

Journal of Chemical Research

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“…However the Diels-Alder adduct is predominantly the endo isomer. In this regard, the use of furan derivatives instead of cyclopentadiene affords the exo isomer at very high yield (Li, 2010(Li, , 2011Jarosz et al, 2001). X-ray crystallography confirmed the molecular structure and the atom connectivity for the title compound, as illustrated in Fig.…”

Section: S1 Commentmentioning

confidence: 99%

exo-1,7-Dimethyl-4-phenyl-10-oxa-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

et al. 2013

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The title compound, C16H15NO3, consists of an oxabicycle fused to an N-phenyl-substituted pyrrolidine ring anti to the double bond, affording the exo isomer. In the oxabicycle system, the six-membered ring presents a boat conformation, while the heterocyclic rings show envelope conformations with the O atom projected out of the plane. In the crystal, adjacent molecules are linked via weak C—H⋯O hydrogen bonds, forming chains propagating along the a-axis direction. The chains are linked by C—H⋯π interactions, forming two-dimensional networks lying parallel to the ac plane.

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“…In 2001, Jarosz et al prepared furans bearing modified sugar (DAGA) at 2-or 3-position (56 and 57) that have been used as dienes for a Diels-Alder reaction with N-phenylmaleimide (58) [36].…”

Section: Sugars As Chiral Inductorsmentioning

confidence: 99%

Ultra High Pressure as a Green and Promising Tool in Glycochemistry

Thomassigny¹,

Siñeriz²,

Greck³

et al. 2012

Mini-Reviews in Organic Chemistry

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Pressure is a fundamental parameter which can accelerate reaction rates. The use of ultra high pressure (0.2-2 GPa) in organic chemistry can be particularly efficient, because it can fix problems of reactivity or regio-and stereoselectivity which could appear at ambient pressure, while being considered as an activation tool. The present review points out the last progresses in the area of glycochemistry with this technique. Selective protection or deprotection of the hydroxyl group of saccharides are described, as well as the most studied cycloaddition reactions, leading to the sugar-base structure dihydropyran or employing a sugar to enhance the stereoselectivity of the reaction. The Wittig reaction, homoallylation with allylstannane and aza-Michael reaction are also presented.

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Synthesis of Sugar-Derived 2′- and 3′-Substituted Furans and Their Application in Diels−Alder Reactions

Cited by 14 publications

References 18 publications

Sequential Diels–Alder Reactions in a Conjugated Tetraene System

Sequential Diels–Alder Reactions in a Conjugated Tetraene System

exo-1,7-Dimethyl-4-phenyl-10-oxa-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

Ultra High Pressure as a Green and Promising Tool in Glycochemistry

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Synthesis of Sugar-Derived 2′- and 3′-Substituted Furans and Their Application in Diels−Alder Reactions

Cited by 14 publications

References 18 publications

Sequential Diels–Alder Reactions in a Conjugated Tetraene System

Sequential Diels–Alder Reactions in a Conjugated Tetraene System

exo-1,7-Dimethyl-4-phenyl-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Ultra High Pressure as a Green and Promising Tool in Glycochemistry

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exo-1,7-Dimethyl-4-phenyl-10-oxa-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione