β-Cyclodextrin-Mediated Enantioselective Photochemical Electrocyclization of 1,3-Dihydro-2<i>H</i>-azepin-2-one

Mansour, Ali; Buendia, Julien; Xie, Juan; Brisset, François; Robin, Sylvie; Naoufal, Daoud; Yazbeck, Ogaritte; Aitken, David J.

doi:10.1021/acs.joc.7b01300

Cited by 11 publications

(7 citation statements)

References 46 publications

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“…Aitken and co-workers reported the photochemical 4 pi-electrocyclization of lactam 47 assisted by heterogenous βcyclodextrin (β-CD) (Figure 7a). 95 The chiral β-CD formed a 1:1 complex with 47 in the solid state, and upon UV irradiation product 48 was obtained in 79% yield and 38% ee. Supramolecular hosts can also promote steric control in bimolecular photochemical reactions.…”

Section: Photochemical Reactivity Enabled By Supramolecular Hostsmentioning

confidence: 99%

Advances in supramolecular host-mediated reactivity

et al. 2020

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Since the trailblazing discoveries of Lehn, Cram and Pedersen, supramolecular chemistry has established itself as a cornerstone of organic chemistry. Supramolecular hosts offer defined microenvironments that mimic the active sites of enzymes, utilizing specific host-guest interactions to enable remarkable rate enhancements and product selectivity. The development of a diverse array of self-assembled hosts, coupled with the increased demand for shorter and greener synthetic routes, have spurred significant progress in the field of supramolecular catalysis. This review covers recent advances in the field, ranging from novel organic reactivity aided by supramolecular hosts to catalytic cooperation between hosts and organometallic compounds or metal nanoparticles. Strides have also been made in the synthetic application of these hosts in siteselective substrate modifications and challenging photochemical reactions. These efforts have enabled the incorporation of non-covalent macromolecular catalysis in natural product syntheses, evidencing their unique advantages as a synthetic tool, and their powerful potential for practical applications.

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Section: Photochemical Reactivity Enabled By Supramolecular Hostsmentioning

confidence: 99%

Advances in supramolecular host-mediated reactivity

et al. 2020

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“…However, in many cases when β-cyclodextrin is used, the inclusion complexes are less soluble and the corresponding suspensions, powders or films are irradiated. In this context, a suspension of the 1:1 complex of β-cyclodextrin and the azepinone 64 has been irradiated with UV light (Scheme 1.14) [71]. The photochemical product 65 was hydrogenated and the corresponding bicyclic γbutyrolactam 66 was isolated in good yields and moderate enantioselectivity.…”

Section: Crystalline Inclusion Complexesmentioning

confidence: 99%

Heterocyclic Compounds in Enantioselective Photochemical Reactions

Hoffmann¹

2022

Heterocycles

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“…Cyclodextrins are frequently studied as host structure for inclusion complexes [35,[141][142][143]. The unsaturated lactam 76 forms an inclusion complex with β-cyclodextrin (Scheme 18) [144]. The 1:1 complex is obtained as a water insoluble powder.…”

Section: Inclusion Structuresmentioning

confidence: 99%

Enantioselective synthesis of heterocyclic compounds using photochemical reactions

Hoffmann

2021

Photochem Photobiol Sci

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Different methods for the direct enantioselective photochemical synthesis of heterocycles are presented. Currently, asymmetric catalysis with templates involving hydrogen bonds or metal complexes is intensively investigated. Enzyme catalysis can be simplified under photochemical conditions. For example, in multi enzyme systems, one or more enzyme catalytic steps can be replaced by simple photochemical reactions. Chiral induction in photochemical reactions performed with homochiral crystals is highly efficient. Such reactions can also be carried out with crystalline inclusion complexes. Inclusion of a photochemical substrate and an enantiopure compound in zeolites also leads to enantioselective compounds. In all these methods, the conformational mobility of the photochemical substrates is reduced or controlled. Memory of chirality is a particular case in which a chiral information is temporally lost but the rigid conformations stabilize the molecular structure which leads to the formation of enantiopure compounds. Such studies allows a profound understanding on how particular conformations determine the configuration of the final products.

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β-Cyclodextrin-Mediated Enantioselective Photochemical Electrocyclization of 1,3-Dihydro-2H-azepin-2-one

Cited by 11 publications

References 46 publications

Advances in supramolecular host-mediated reactivity

Advances in supramolecular host-mediated reactivity

Heterocyclic Compounds in Enantioselective Photochemical Reactions

Enantioselective synthesis of heterocyclic compounds using photochemical reactions

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