Electrophilic Bromolactonization of Cyclopropyl Diesters Using Lewis Basic Chalcogenide Catalysts

Gieuw, Matthew H.; Leung, Vincent Ming-Yau; Ke, Zhihai; Yeung, Ying‐Yeung

doi:10.1002/adsc.201800886

Cited by 25 publications

(8 citation statements)

References 52 publications

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“…Yeung and co-workers reported switchable syn/anti selective bromolactonizations of cyclopropyl diesters 39 [66]. The use of cyclopropanes as substrates in bromocyclizations is noteworthy in this study, in which the chalcogenide catalysts, Ph3PS and Ph2PSe, play important roles in the activation of the cyclopropane moiety in the substrates.…”

Section: Syn/anti Selective Cyclizationsmentioning

confidence: 80%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

China

Kumar

Kikushima

et al. 2020

Preprint

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In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties via the generation of halonium intermediates, followed by the attack of carbon-, nitrogen-, oxygen-, and sulfur-containing nucleophiles to give highly functionalized carbo- and heterocycles. Interestingly, new transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products according to the difference in the size and number of halogen atoms have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis.

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Section: Syn/anti Selective Cyclizationsmentioning

confidence: 80%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

China

Kumar

Kikushima

et al. 2020

Preprint

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“…[148,149] However, this strategy has limited application in bromolactonization of alkenes, which also presents shortcomings like regioselectivity, dihalogenation and poor yields. [150][151][152][153][154] Thereby, in 2019, an efficient and regioselective strategy was reported by Hansen et. al., [155] for bromolactonization.…”

Section: Organoselenium Reagents As Regioselective and Stereoselectivmentioning

confidence: 99%

“…The authors proposed a mechanistic Even with the advent of chiral organoselenium catalysts, its application in asymmetric bromolactonization is underexplored although work has been done on achiral selenium-catalyzed bromolactonization. [150][151][152][153][154][155] Taking it further, Shivakawa et al, [156] achieved enantioselective bromolactonization of alkenes 78 & 80 to give γ-butyrolactone derivatives 79 & 81 in the presence of BINOL-derived chiral bifunctional selenide catalysts 82d & 82c at À 78°C respectively (Scheme 34). The presence of OH group in the catalyst was found to be pivotal for conferring enantioselectivity to the reaction.…”

Section: Organoselenium Reagents As Regioselective and Stereoselectivmentioning

confidence: 99%

“…Organoselenium compounds were found to catalyze the formation of active halogenium intermediate that can be transferred to alkenes [148,149] . However, this strategy has limited application in bromolactonization of alkenes, which also presents shortcomings like regioselectivity, dihalogenation and poor yields [150–154] . Thereby, in 2019, an efficient and regioselective strategy was reported by Hansen et.…”

Section: Overview On Selenium‐catalyzed/selenium Incorporating Transfmentioning

confidence: 99%

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Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

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The ever-growing interest for organoselenium compounds amongst the chemists has made commendable impact in the field of medicinal chemistry, material chemistry, chemical biology and biochemistry. Researchers have progressively contributed in the development of organoselenium compounds over the years which has been periodically reviewed. On the similar note, this review attempts at providing an overview of the recent advances made in organoselenium chemistry while covering their catalytic indulgence in different transformational approaches, their role in asymmetric synthesis, and synthetic approaches steering their synthesis. These approaches encompass selenofunctionalization and/or cyclization, electrochemical selenylation, bromolactonization, [2,3]-or [1,2]-sigmatropic rearrangement reactions among others. Herein, we have focused on the synthetic approaches developed for the past three years that have not been covered in previously reviewed scientific material. With the knowledge of the recent progress covered, this review could contribute towards future development of organoselenium compounds along with the improvement of the current status.

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“…Yeung and co-workers reported switchable syn / anti selective bromolactonizations of cyclopropyl diesters 39 [ 65 ]. The use of cyclopropanes as substrates in bromocyclizations is noteworthy in this study in which the chalcogenide catalysts, Ph 3 PS and Ph 2 PSe, play important roles in the activation of the cyclopropane moiety in the substrates.…”

Section: Reagent-switchable Cyclizationsmentioning

confidence: 99%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

et al. 2020

View full text Add to dashboard Cite

In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties by generating halonium intermediates, followed by the attack of carbon-containing, nitrogen-containing, oxygen-containing, and sulfur-containing nucleophiles to give highly functionalized carbocycles and heterocycles. New transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products, according to the difference in the size and number of halogen atoms, have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis.

show abstract

Electrophilic Bromolactonization of Cyclopropyl Diesters Using Lewis Basic Chalcogenide Catalysts

Cited by 25 publications

References 52 publications

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

Insights into the Recent Synthetic Advances of Organoselenium Compounds

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

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