Enantioselektive Lewis‐Säure‐katalysierte <i>ortho</i>‐Photocycloaddition von Phenanthren‐9‐carbaldehyden

Stegbauer, Simone; Jandl, Christian; Bach, Thorsten

doi:10.1002/ange.201808919

Cited by 22 publications

(7 citation statements)

References 46 publications

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“…Nevertheless, this strategy has been applied only to heteroaromatic scaffolds, often in combination with the use of UV light [74] . On the other hand, visible light‐dearomatization of benzene derivatives has been accomplished only through cyclobutane formation (Scheme 25a) [75] . Therefore, the development of new [2+2]‐heterocycloaddition processes for the dearomatization of such class of compounds it is highly desirable and still represents an open synthetic challenge (Scheme 25b).…”

Section: Discussionmentioning

confidence: 99%

Mechanisms and Synthetic Strategies in Visible Light‐Driven [2+2]‐Heterocycloadditions

et al. 2023

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The synthesis of four membered heterocycles usually requires multi-step procedures and prefunctionalized reactants. A straightforward alternative is the photochemical [2+2]-heterocycloaddition between an alkene and a carbonyl derivative, conventionally based on the photoexcitation of this latter. However, this approach is limited by the absorption profile of the carbonyl, requiring in most of the cases the use of high-energy UV-light, that often results in undesired side reactions and/or the degradation of the reaction components. The development of new and milder visible light-driven [2+2]-heterocycloadditions is, therefore, highly desirable. In this Review, we highlight the most relevant achievements in the development of [2+2]-heterocycloadditions promoted by visible light, with a particular emphasis on the involved reaction mechanisms. The open challenges will also be discussed, suggesting new possible evolutions, and stimulating new methodological developments in the field. Mechanisms for Visible Light [2+2]-Hetero-CycloadditionsA prerequisite for visible light [2+2]-heterocycloadditions is the presence of a photoactive species able to absorb light

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Section: Discussionmentioning

confidence: 99%

Mechanisms and Synthetic Strategies in Visible Light‐Driven [2+2]‐Heterocycloadditions

et al. 2023

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“…The closest result we have obtained so far relates to work performed by Simone Stegbauer on phenanthrene-9-carboxaldehydes (Scheme 23 ). 52 Employing a chiral Lewis acid, specifically the activated oxazaborolidine 58 , it was possible to involve the parent compound 57 in an intermolecular ortho photocycloaddition to 2,3-dimethyl-2-butene. Upon visible-light irradiation, the desired product 59 was isolated in a good yield with high enantioselectivity.…”

Section: Perspective and Summarymentioning

confidence: 99%

The Awakening of a Sleeping Beauty: The ortho Photocycloaddition in the Total Synthesis of Protoilludane- and Prezizaene-Type Sesquiterpenes

Bach¹,

Gilbert²

2022

Synlett

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Photochemical cascade (domino) reactions provide a unique opportunity for the construction of complex molecular architectures. Specifically, an intramolecular ortho photocycloaddition of 7-(alkenyloxy)-indanones triggers a sequence of consecutive reactions that can lead in a single operation to the complete skeleton of two important classes of sesquiterpenes: protoilludanes and prezizaenes. In the former case, two transformations follow the initial photocycloaddition, while in the latter case, there are three consecutive transformations, two of which are initiated by a photon. Remarkably, the reaction cascades proceed with exquisite diastereoselectivity, generating three (protoilludane) or five (prezizaene) stereogenic centers with defined relative configurations.1 Introduction2 First Encounter and Initial Studies3 Protoilludane-Type Sesquiterpenes4 Prezizaene-Type Sesquiterpenes5 Enantioselectivity6 Perspective and Summary

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“…In 2018, Bach et al [102] . reported the enantioselective photocatalytic cycloaddition reaction of phenanthrene‐9‐formaldehyde to alkene.…”

Section: Combining Lewis Acid Catalysis With Photoredox Catalysismentioning

confidence: 99%

Advanced Synthesis Using Photocatalysis Involved Dual Catalytic System

Guo

Wang

et al. 2022

Eur J Org Chem

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Combining visible‐light photoredox catalysis with other kinds of catalysis is a powerful strategy to address the barriers met in reactions driven by single catalyst. Under environmentally benign condition, photoredox catalysis produces radical species via visible light irradiation. These species then work with other catalysts, often resulting in unconventional reactivities, by which the scope of reaction could be expanded. Interest focusing on photocatalysis in the synthetic chemistry community has grown tremendously over the past five years, and one of the most striking emerging features is the development of dual catalytic approaches. This minireview summarizes the progress on this theme, mainly including dual catalytic systems merging photoredox activation with acid/base catalysts.

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Enantioselektive Lewis‐Säure‐katalysierte ortho‐Photocycloaddition von Phenanthren‐9‐carbaldehyden

Cited by 22 publications

References 46 publications

Mechanisms and Synthetic Strategies in Visible Light‐Driven [2+2]‐Heterocycloadditions

Mechanisms and Synthetic Strategies in Visible Light‐Driven [2+2]‐Heterocycloadditions

The Awakening of a Sleeping Beauty: The ortho Photocycloaddition in the Total Synthesis of Protoilludane- and Prezizaene-Type Sesquiterpenes

Advanced Synthesis Using Photocatalysis Involved Dual Catalytic System

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Enantioselektive Lewis‐Säure‐katalysierte ortho‐Photocycloaddition von Phenanthren‐9‐carbaldehyden

Cited by 22 publications

References 46 publications

Mechanisms and Synthetic Strategies in Visible Light‐Driven [2+2]‐Heterocycloadditions

Mechanisms and Synthetic Strategies in Visible Light‐Driven [2+2]‐Heterocycloadditions

The Awakening of a Sleeping Beauty: The ortho Photocycloaddition in the Total Synthesis of Protoilludane- and Prezizaene-Type ­Sesquiterpenes

Advanced Synthesis Using Photocatalysis Involved Dual Catalytic System

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The Awakening of a Sleeping Beauty: The ortho Photocycloaddition in the Total Synthesis of Protoilludane- and Prezizaene-Type Sesquiterpenes