Novel methods for the synthesis of three-, four-, five-, six- and seven-membered, saturated and partially unsaturated carbocycles

Hartley, Richard C.; Caldwell, Stuart T.

doi:10.1039/a804421j

Cited by 82 publications

(13 citation statements)

References 202 publications

(172 reference statements)

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“…2,5,[16][17][18][19][20] Two comprehensive reviews summarizing these developments over the last 10 years deserve special attention, 9,21 as they are not restricted to (organo)catalytic procedures. 2,5,[16][17][18][19][20] Two comprehensive reviews summarizing these developments over the last 10 years deserve special attention, 9,21 as they are not restricted to (organo)catalytic procedures.…”

Section: Background To Cyclopropane Synthesismentioning

confidence: 99%

Cyclopropanation Reactions☆

Arvidsson¹,

Bose²,

Naicker³

2015

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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All other uses, reproduction and distribution, including without limitation commercial reprints, selling or licensing copies or access, or posting on open internet sites, your personal or institution's website or repository, are prohibited. For exceptions, permission may be sought for such use through Elsevier's permissions site at: http://www.elsevier.com/locate/permissionusematerial Arvidsson P.I., Bose P.P. and Naicker T. (2014) Cyclopropanation Reactions. In: Reedijk, J. (Ed.) Elsevier Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Waltham, MA: Elsevier. 23-Jan-15

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Section: Background To Cyclopropane Synthesismentioning

confidence: 99%

Cyclopropanation Reactions☆

Arvidsson¹,

Bose²,

Naicker³

2015

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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“…[1] Development of facile cyclization reactions which allow rapid construction of five-membered carbocyclic frameworks has thus attracted immense interest in the synthetic community. Silver(I)catalyzed intramolecular arene trapping of the resulting cyclic oxyallyl cation leads to formation of tricyclic indolinefused cyclopentanone.…”

mentioning

confidence: 99%

“…[1] Development of facile cyclization reactions which allow rapid construction of five-membered carbocyclic frameworks has thus attracted immense interest in the synthetic community. [1] Development of facile cyclization reactions which allow rapid construction of five-membered carbocyclic frameworks has thus attracted immense interest in the synthetic community.…”

mentioning

confidence: 99%

Interrupted Imino‐Nazarov Cyclization of 1‐Aminopentadienyl Cation and Related Cascade Process

et al. 2014

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Facile 4π conrotatory imino-Nazarov cyclization of a 1-aminopentadienyl cation generated from condensation an aldehyde and secondary aniline in the presence of a catalytic amount of a Lewis acid has been developed. Silver(I)-catalyzed intramolecular arene trapping of the resulting cyclic oxyallyl cation leads to formation of tricyclic indoline-fused cyclopentanone. The use of lanthanide salts allows transformation after the initial trapping to afford tetrahydroquinoline-fused cyclopentenone in a concise manner.

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“…The use of lanthanide salts allows transformation after the initial trapping to afford tetrahydroquinoline-fused cyclopentenone in a concise manner.Five-membered carbocyclic scaffolds are ubiquitous in both natural products and biologically important molecules. [1] Development of facile cyclization reactions which allow rapid construction of five-membered carbocyclic frameworks has thus attracted immense interest in the synthetic community. In this context, the classical Nazarov reaction, involving 4pe À conrotatory electrocyclization of pentadienyl cation, arguably represents one of the most efficient methods to access a diverse array of carbocycles.…”

mentioning

confidence: 99%

Interrupted Imino‐Nazarov Cyclization of 1‐Aminopentadienyl Cation and Related Cascade Process

William¹,

Wang²,

Ding³

et al. 2014

Angewandte Chemie

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Facile 4p conrotatory imino-Nazarov cyclization of a 1-aminopentadienyl cation generated from condensation an aldehyde and secondary aniline in the presence of a catalytic amount of a Lewis acid has been developed. Silver(I)catalyzed intramolecular arene trapping of the resulting cyclic oxyallyl cation leads to formation of tricyclic indolinefused cyclopentanone. The use of lanthanide salts allows transformation after the initial trapping to afford tetrahydroquinoline-fused cyclopentenone in a concise manner.Five-membered carbocyclic scaffolds are ubiquitous in both natural products and biologically important molecules. [1] Development of facile cyclization reactions which allow rapid construction of five-membered carbocyclic frameworks has thus attracted immense interest in the synthetic community. In this context, the classical Nazarov reaction, involving 4pe À conrotatory electrocyclization of pentadienyl cation, arguably represents one of the most efficient methods to access a diverse array of carbocycles. [2] The synthetic utility of the Nazarov cyclization is further enhanced by the possibility of trapping the oxyallyl cation with nucleophiles both intra-and intermolecularly in a process termed the interrupted Nazarov reaction. [3] Recent years have seen a wide range of nucleophiles being employed to capture the cation, thus rendering the formation of highly functionalized cyclopentanones as well as intriguing polycyclic skeletons which contain five-membered carbocycles. [4] A relatively new variant of the Nazarov reaction which has received less attention is the imino-Nazarov cyclization, which essentially involves electrocyclic ring closure of the pentadienyl system bearing an imino group instead of the conventional ketone functionality. Since the pioneering work reported by Tius et al. on the lithiated imino-Nazarov reaction, [5] literature examples pertaining to this special class of Nazarov reaction remain scarce. The lack of success in developing an imino-Nazarov cyclization stems from the inherent challenge associated with higher stability of the pentadienyl cation, relative to the corresponding cyclic allyl cation, owing to stabilization by a nitrogen atom. [6] Later, Tius and co-workers disclosed the use of enamine-iminium ion formation in facilitating an imino-Nazarov cyclization. [7] The work of Hsung and co-workers on gold-catalyzed cyclization of allenamides demonstrated that diminishing nitrogen stabilization through incorporation of an electron-withdrawing tosyl group proved to be an effective solution to drive the electrocyclization forward. [8] More recently, the group of West reported silver-assisted ring opening of 2,2-dichlorocyclopropanes to access a 3-aminopentadienyl cation capable of undergoing imino-Nazarov cyclization, including a few examples of interrupted process (Scheme 1). [9] Our recent interest in the synthesis of cyclopentanoid compounds [10] prompted us to investigate the possibility of a diene iminium ion, of the type shown in Scheme 1, to undergo an imino-Nazarov cycl...

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Novel methods for the synthesis of three-, four-, five-, six- and seven-membered, saturated and partially unsaturated carbocycles

Cited by 82 publications

References 202 publications

Cyclopropanation Reactions☆

Cyclopropanation Reactions☆

Interrupted Imino‐Nazarov Cyclization of 1‐Aminopentadienyl Cation and Related Cascade Process

Interrupted Imino‐Nazarov Cyclization of 1‐Aminopentadienyl Cation and Related Cascade Process

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