Regio‐ und stereoselektive Photocycloadditionen aromatischer Aldehyde an Furan und 2,3‐Dihydrofuran

Griesbeck, Axel G.; Stadtmüller, Stefan

doi:10.1002/cber.19901230222

Cited by 64 publications

(21 citation statements)

References 34 publications

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“…Therefore, the oxetanes 99a,b are the only products isolated from the reaction of dihydrofurane 100 with benzaldehyde 101 (Scheme 17). 78 No electron transfer is involved in the formation of this isomer. 79 The formation of a solvent separated ion pair is endothermic (Get = +0.62 eV).…”

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confidence: 99%

Studies in organic and physical photochemistry – an interdisciplinary approach

Oelgemöller

Hoffmann

2016

Org. Biomol. Chem.

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Traditionally, organic photochemistry when applied to synthesis strongly interacts with physical chemistry. The aim of this review is to illustrate this very fruitful interdisciplinary approach and cooperation. A profound understanding of the photochemical reactivity and reaction mechanisms is particularly helpful for optimization and application of these reactions. Some typical reactions and particular aspects are reported such as the Norrish-Type II reaction and the Yang cyclization and related transformations, the [2 + 2] photocycloadditions, particularly the Paternò-Büchi reaction, photochemical electron transfer induced transformations, different kinds of catalytic reactions such as photoredox catalysis for organic synthesis and photooxygenation are discussed. Particular aspects such as the structure and reactivity of aryl cations, photochemical reactions in the crystalline state, chiral memory, different mechanisms of hydrogen transfer in photochemical reactions or fundamental aspects of stereoselectivity are discussed. Photochemical reactions are also investigated in the context of chemical engineering. Particularly, continuous flow reactors are of interest. Novel reactor systems are developed and modeling of photochemical transformations and different reactors play a key role in such studies. This research domain builds a bridge between fundamental studies of organic photochemical reactions and their industrial application.

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confidence: 99%

Studies in organic and physical photochemistry – an interdisciplinary approach

Oelgemöller

Hoffmann

2016

Org. Biomol. Chem.

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“…The selectivities were nearly identical to those with the unsubstituted 2,3-dihydrofuran as alkene component (88 : 12 and 90 : 10, respectively [16]). …”

Section: Resultsmentioning

confidence: 65%

Spin‐dependent diastereoselectivity in the photocycloaddition of aldehydes to 2,2‐dimethyl‐2,3‐dihydrofuran

Bondock¹,

Griesbeck

2005

International Journal of Photoenergy

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“…[40] In this respect, the 2,3-dihydropyrroles are apparently more closely related to 2,3-dihydrofurans, which undergo the photocycloaddition smoothly and with high simple diastereoselectivity. [41,42] If this analogy is true, the six-membered tetrahydropyridines should react more sluggishly than do the six-membered dihydropyrans. [40] Indeed, the substrate 21 gave only poor yields of photocycloadduct 22 (Scheme 7) under a variety of conditions.…”

Section: Resultsmentioning

confidence: 99%

The Synthesis of (+)-Preussin and Related Pyrrolidinols by Diastereoselective Paternò-Büchi Reactions of Chiral 2-Substituted 2,3-Dihydropyrroles

2000

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The N-alkoxycarbonyl substituted 2,3-dihydropyrroles 3 and 8 are converted to 2-benzyl-3-pyrrolidinols by the Paternò - Büchi reaction followed by hydrogenolysis. Since the addition of the photoexcited benzaldehyde at the unsaturated heterocycle proceeds in a syn fashion, the benzyl group at C-2 and the hydroxy group at C-3 of the product are cis oriented. The simple and facial diastereoselectivities of the Paternò-Büchi reaction were studied more closely and the relative configuration of the products was elucidated. The thermodynamically less stable endo product is formed as a result of simple diastereoselection. The face differentiation in 2-substituted 2,3-dihydropyrroles is presumably due to the nonplanarity of these heterocycles, which forces attack of the carbonyl group on the face with the existing substituent. All-cis-pyrrolidinols are consequently formed after hydrogenolysis. Following this route, a total synthesis of the pyrrolidinol alkaloid (+)-preussin (1) was conducted, which yielded the target compound in a total yield of 11% over nine steps starting from L-pyroglutaminol (11).

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Regio‐ und stereoselektive Photocycloadditionen aromatischer Aldehyde an Furan und 2,3‐Dihydrofuran

Cited by 64 publications

References 34 publications

Studies in organic and physical photochemistry – an interdisciplinary approach

Studies in organic and physical photochemistry – an interdisciplinary approach

Spin‐dependent diastereoselectivity in the photocycloaddition of aldehydes to 2,2‐dimethyl‐2,3‐dihydrofuran

The Synthesis of (+)-Preussin and Related Pyrrolidinols by Diastereoselective Paternò-Büchi Reactions of Chiral 2-Substituted 2,3-Dihydropyrroles

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