Vierringsynthesen durch photosensibilisierte Cycloaddition von Dimethylmaleinsäureanhydrid an Olefine

Schenck, Günther O.; Hartmann, Willy; Steinmetz, Reinhard

doi:10.1002/cber.19630960222

Cited by 122 publications

(37 citation statements)

References 9 publications

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“…While the reaction of 2furylmethanol with benzophenone showed low regioselectivity, the presence of larger substituents on the carbon bearing the alcoholic function allows a high regioselectivity (Scheme 7) [37]. Furthermore, when 2-furylethanol (20) was used as substrate, a 1 : 1 mixture of stereoisomers was obtained, while, when 1-(2-furyl)-benzylic alcohol (21) was the substrate, only one diastereoisomer was obtained. The high diastereoselectivity observed was confirmed using optically active 21.…”

Section: Photoaddition Of Carbonyl Compounds To Chiral Furansmentioning

confidence: 99%

Regio‐ and stereoselectivity in the Paternò‐Büchi reaction on furan derivatives

D’Auria

Emanuele

Racioppi

2006

International Journal of Photoenergy

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The photochemical coupling reaction between 2,3-dihydrofuran and benzaldehyde was studied by using DFT/B3LYP/6 − 31G + (d, p) method. The regiocontrol of the attack of the benzaldehyde on the double bond is related to the different stabilities of the biradical intermediates. The endo stereoselectivity of the reaction depends on the superposition between HSOMO and LSOMO in the biradical intermediate. In the photochemical reaction between furan and benzaldehyde also the regiocontrol depends on the relative stability of the possible biradical intermediates. The exo stereoselectivity of the coupling reaction depends on the superposition between the HSOMO and LSOMO of the biradical intermediate. The reaction of chiral phenylglyoxylates with furan gave the corresponding adducts with de = 15-95%. The stereocontrol can be explained considering the energy gap between the biradical intermediates in the coupling reaction. When the reaction was performed in the presence of zeolite, the diastereoisomeric excess increased. The reaction of benzoin and 2-phenylpropiophenone with furan gave the cycloadduct with high diastereocontrol.All the products were obtained with de > 98%. The Paterrnò-Büchi reaction between 2-furylmethanols with aromatic carbonyl compounds also showed high regio-and stereocontrol. On the contrary, when 5-methyl derivatives were used, a lack of regiocontrol was observed. Furthermore, with aliphatic carbonyl compounds, no diastereoselectivity was observed. These results were explained assuming the attack of the excited carbonyl compound on the same side as the hydroxyl group, through the formation of a hydrogen bond or of a complex. This type of attack gave the biradical intermediate in preferential conformations. The relative energies of these conformers account for the observed diastereoselectivity.

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Section: Photoaddition Of Carbonyl Compounds To Chiral Furansmentioning

confidence: 99%

Regio‐ and stereoselectivity in the Paternò‐Büchi reaction on furan derivatives

D’Auria

Emanuele

Racioppi

2006

International Journal of Photoenergy

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“…181 Another class of synthetically relevant alkene components which react this way are five-membered heterocycles such as furan (97). 182 The major product from its addition to aldehydes, e.g. nonanal (96), were exo-products, e.g.…”

Section: Scheme 37mentioning

confidence: 99%

Stereoselective Intermolecular [2 + 2]-Photocycloaddition Reactions and Their Application in Synthesis

Bach

1998

Synthesis

300

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Stereoselective intermolecular [2+2]-photocycloaddition reactions of alkenes and Paternò-Büchi reactions are reviewed. For both reactions the regioselectivity and the simple diastereoselectivity which are relevant to the formation of a single product isomer are explained based on representative examples. In the subsequent sections the facial diastereoselectivity induced by the respective reaction partner is treated. Particular emphasis is given on synthetic applications of the cyclobutanes and oxetanes obtained by the photochemical key step. Consecutive reactions are discussed and the potential use of the four-membered ring intermediates is highlighted.

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“…Schenck reported that the irradiation of benzophenone in furan gave the corresponding adduct in 94% yield (Scheme 27) [135]. The structure was confirmed by Gagnaire et al [136].…”

Section: Reactions With Heterocyclic Compoundsmentioning

confidence: 76%

Oxetane Synthesis through the Paternò-Büchi Reaction

D’Auria

Racioppi

2013

Molecules

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Abstract:The Paternò-Büchi reaction is a photochemical reaction between a carbonyl compound and an alkene to give the corresponding oxetane. In this review the mechanism of the reaction is discussed. On this basis the described use in the reaction with electron rich alkenes (enolethers, enol esters, enol silyl ethers, enanines, heterocyclic compounds has been reported. The stereochemical behavior of the reaction is particularly stressed. We pointed out the reported applications of this reaction to the synthesis of naturally occuring compounds.

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Vierringsynthesen durch photosensibilisierte Cycloaddition von Dimethylmaleinsäureanhydrid an Olefine

Cited by 122 publications

References 9 publications

Regio‐ and stereoselectivity in the Paternò‐Büchi reaction on furan derivatives

Regio‐ and stereoselectivity in the Paternò‐Büchi reaction on furan derivatives

Stereoselective Intermolecular [2 + 2]-Photocycloaddition Reactions and Their Application in Synthesis

Oxetane Synthesis through the Paternò-Büchi Reaction

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