Synthesis of (+)-Greek Tobacco Lactone via a Diastereoablative Epoxidation and a Selenium-Catalyzed Oxidative Cyclization

Leisering, Stefan; Riaño, Iker; Depken, Christian; Gross, Leona J.; Weber, Manuela; Lentz, Dieter; Zimmer, Reinhold; Stark, Christian B. W.; Breder, Alexander; Christmann, Mathias

doi:10.1021/acs.orglett.7b00484

Cited by 26 publications

(13 citation statements)

References 39 publications

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“…Considering the fact that the use of NFSI (2) as the terminal oxidant only led to moderate enantiomeric ratios, we turned our attention to a more generalized enantioselective selenocatalytic oxidation concept that-in the long run-potentially allowed for a broader scope of coupling partners to simple alkenes. Recently, our group disclosed a light-driven dual catalytic protocol that enabled for the first time the use of ambient air as the terminal oxidant in selenium-π-acid-catalyzed allylic alkene functionalizations [24][25][26][27][28]. A key asset of this strategy is the circumstance that various nucleophilic reaction partners, such as carboxylic acids, alcohols, and hydrogen phosphates, are compatible with aerobic conditions.…”

Section: Methodsmentioning

confidence: 99%

Rational Design of Chiral Selenium-π-Acid Catalysts

et al. 2019

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A series of unprecedented chiral selenium-π-acid catalysts for the asymmetric, oxidative functionalization of alkenes has been developed. In total, eleven different chiral dihydrodiselenocine and (di-)alkoxyphenyl (di)selenide motifs have been synthesized in a concise, modal, and straightforward fashion. Commercially available, non-racemic alcohols have been predominantly used as chiral building blocks for the facile assembly of the selenium-π-acid catalysts. These species have been exemplarily applied to the enantioselective intermolecular imidation and intramolecular acyloxylation of two olefins using N-fluorobenzenesulfonimide (NFSI) and ambient air, respectively, as terminal oxidants. In part, the catalysts provide very good yields of up to 99% and enantiomeric ratios of up to 83.5:16.5 under aerobic conditions.

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Section: Methodsmentioning

confidence: 99%

Rational Design of Chiral Selenium-π-Acid Catalysts

et al. 2019

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“…Subsequently, Breder and co‐workers extended their dual photoredox selenium‐π‐acid catalysis concept to other coupling processes, such as lactonizations, allylic etherifications, and phosphatations of simple olefins (Scheme B–D) –. The last transformation is particularly noteworthy, as it represents the first catalytic example of an allylic oxidative coupling of non‐activated hydrogen phosphates with simple alkenes 71 under aerobic conditions.…”

Section: Redox Neutral and Oxidative C−c π‐Bond Functionalizationsmentioning

confidence: 99%

Light‐Driven Single‐Electron Transfer Processes as an Enabling Principle in Sulfur and Selenium Multicatalysis

Breder

Depken²

2019

Angew Chem Int Ed

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Cooperativity has become a mainstay in the context of multicatalytic reaction design. The combination of two or more catalysts that possess mechanistically distinct activation principles within a single chemical setting can enable bond constructions that would be impossible for any of the catalysts alone. An emerging subdomain within the field of multicatalysis is characterized by single‐electron transfer processes that are sustained by the synergistic merger of sulfur or selenium organocatalysis with photoredox catalysis. From a synthetic viewpoint, such processes have tremendous value, as they can offer new and economic pathways for the concise assembly of complex molecular architectures. Thus, the aim of this Review is to highlight recent methodological progress made in this area and to contextualize representative transformations with the mechanistic underpinnings that enable these reactions.

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“…In der Folgezeit weiteten Breder et al. ihr duales Photoredox/Selen‐π‐Säure‐Katalysekonzept auf andere aerobe Kupplungsreaktionen wie beispielsweise Lactonisierungen, allylische Veretherungen und Phosphatierungen aus –. Hinsichtlich der letztgenannten Transformation ist hervorzuheben, dass sie das erste katalytische Beispiel für eine allylische oxidative Kupplung nicht‐aktivierter Hydrogenphosphate mit einfachen Alkenen 71 unter aeroben Bedingungen darstellt.…”

Section: Redoxneutrale Und Oxidative C‐c‐π‐bindungsfunktionalisierungenunclassified

Lichtgetriebene Ein‐Elektronen‐Transferprozesse als Funktionsprinzip in der Schwefel‐ und Selen‐Multikatalyse

Breder

Depken²

2019

Angewandte Chemie

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Das Prinzip der Kooperativität stellt inzwischen einen Grundpfeiler im Bereich der Multikatalyse dar. Durch die Kombination zweier oder mehrerer Katalysatoren mit mechanistisch unterschiedlichen Aktivierungsmodi, die gemeinsam chemische Prozesse vorantreiben, werden zuweilen Bindungsknüpfungen ermöglicht, zu denen keiner der beteiligten Katalysatoren einzeln imstande wäre. Ein stetig wachsender Teilbereich der Multikatalyse befasst sich mit lichtgetriebenen Ein‐Elektronen‐Transferprozessen, die durch die synergistische Verzahnung von Schwefel‐ oder Selenkatalysatoren mit Photoredoxkatalysatoren aufrechterhalten werden. Reaktionen, die auf diesem Funktionsprinzip beruhen, bergen ein enormes synthetisches Potential, da sie rasche und hoch ökonomische Zugangswege zu komplexen molekularen Strukturen ermöglichen können. Vor diesem Hintergrund ist das Ziel dieses Aufsatzes, jüngste methodische Entwicklungen auf diesem Gebiet näher zu beleuchten und anhand ausgewählter Beispielreaktionen einen allgemeinen Einblick in ihre mechanistischen Grundlagen zu vermitteln.

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Synthesis of (+)-Greek Tobacco Lactone via a Diastereoablative Epoxidation and a Selenium-Catalyzed Oxidative Cyclization

Cited by 26 publications

References 39 publications

Rational Design of Chiral Selenium-π-Acid Catalysts

Rational Design of Chiral Selenium-π-Acid Catalysts

Light‐Driven Single‐Electron Transfer Processes as an Enabling Principle in Sulfur and Selenium Multicatalysis

Lichtgetriebene Ein‐Elektronen‐Transferprozesse als Funktionsprinzip in der Schwefel‐ und Selen‐Multikatalyse

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