Synthesis of Heterocyclic Compounds by Carbenoid Transfer Reactions

Ferreira, Vı́tor F.

doi:10.2174/138527207779316462

Cited by 49 publications

(10 citation statements)

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“…Indole is electron rich and will typically favor alkylation of the carbenoid at the 3-position [5–8]. Hence, the anticipated initial product from the reaction would be the bottom structure in Scheme 2.…”

Section: Resultsmentioning

confidence: 99%

“…One of the most efficient approaches is the transition metal-catalyzed C–H functionalization by diazo compounds [5–8]. The reactions of indoles with electrophilic metal-bound carbenes, or carbenoids, generated from diazo compounds, takes place under mild reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

“…Electron-rich indoles typically give selective alkylation at the C3 position in the absence of a preexisting C3-substituent. In the presence of a C3-substituent, the alkylation is usually directed to the C2-position [5–8]. Electron-withdrawing groups (acyl, carbamoyl) at the indole nitrogen typically lead to cyclopropanation products that can be purified and isolated.…”

Section: Introductionmentioning

confidence: 99%

“…Electron-withdrawing groups (acyl, carbamoyl) at the indole nitrogen typically lead to cyclopropanation products that can be purified and isolated. Several reaction pathways have been proposed to account for the observed reactivity, but the mechanism for many of the reactions between indoles and metal-bound carbenes are unclear [5–8]. …”

Section: Introductionmentioning

confidence: 99%

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Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates

Mortén¹,

Hennum²,

Bonge‐Hansen³

2015

Beilstein J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates

Mortén¹,

Hennum²,

Bonge‐Hansen³

2015

Beilstein J. Org. Chem.

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“…B. Cyclopropanierung von Olefinen; C,H-, O,H-und N,H-Insertion; Bildung von Yliden und formalen Carbendimeren). [2,3] Unter dem Einfluss von Protonen bilden sich aliphatische Diazoniumionen, was Diazoverbindungen zu Vorstufen bzw. Syntheseäquivalenten von Carbokationen macht.…”

Section: Introductionunclassified

Neues zur Synthese von Diazoverbindungen

Maas

2009

Angewandte Chemie

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Aufgrund der vielseitigen und nützlichen Folgechemie von Diazoverbindungen (R1R2CN2) ist das Interesse an dieser Substanzklasse seit Jahren ungebrochen. Dabei wird auch das bereits vorhandene Methodenrepertoire zur Herstellung von Diazoverbindungen immer wieder um neue Verfahren oder um neuartige Varianten etablierter Synthesewege ergänzt. Nicht selten tragen die neuen Synthesevorschläge der Labilität und beachtlichen chemischen Reaktivität bestimmter Typen von Diazoverbindungen Rechnung, aber auch dem Aspekt umweltfreundlicherer Methodik wurde Beachtung geschenkt.

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Catalytic, Asymmetric, Intramolecular Carbon–Hydrogen Insertion

2012

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The insertion of a chiral‐ligated metal carbene into an aliphatic C‐H bond to construct a carbon‐carbon bond imparts asymmetry into the resultant molecule to form enantiomerically enriched lactones, lactams, and cycloalkane derivatives and returns the chiral‐ligated metal to its catalytically active state. Insertion is favored by electron‐donating groups adjacent to the C‐H bond that undergoes insertion, and is disfavored by electron‐withdrawing groups. Chiral dirhodium(II) carboxamidates have proven to have the greatest breadth of high selectivities, but other classes of catalysts are selective in specific cases. Although there are examples of iodonium ylides as reactants, diazo compounds are the reactants of choice for these reactions. Diazocarbonyl compounds, especially diazoacetates and diazoacetamides, have reactivities and selectivities that are most suitable for high product yields and high stereoselectivities. This reaction is optimally designed for the formation of five‐membered ring compounds using diazoacetates and diazoacetamides and of four‐membered ring products with constrained diazoacetamides. Access to lignan lactones, baclofen, deoxyxylolactone, and rolipram, among others, exemplify the efficiencies of this methodology relative to other synthetic approaches.

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Synthesis of Heterocyclic Compounds by Carbenoid Transfer Reactions

Cited by 49 publications

References 88 publications

Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates

Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates

Neues zur Synthese von Diazoverbindungen

Catalytic, Asymmetric, Intramolecular Carbon–Hydrogen Insertion

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