![1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile structure](https://static.chemtradehub.com/structs/143/1434747-57-5-fc0d.webp "1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile structure")
1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile
CAS Number:
1434747-57-5
Molecular Formula:
C21H22BN3O4S
Organocopper triggered cyclization of conjugated dienynes via tandem SN2′/Alder-ene reaction
Literature Information
Publication Date
2017-11-24
DOI
10.1039/C7QO00288B
Impact Factor
5.281
Authors
Tanzeel Arif, Cyril Borie, Marion Jean, Nicolas Vanthuyne, Michèle P. Bertrand, Didier Siri, Malek Nechab
View Original
Abstract
Propargylic carbonates were converted to indenes through a SN2′/Alder-ene cascade triggered by organocopper reagents. The reaction tolerates different organocopper species generated either from organolithiums or Grignard reagents. A catalytic version of this strategy could be devised using either copper or iron catalysts. Attempts to transfer chirality from an enantioenriched substrate revealed a moderate chirality conversion because of a low discrimination between the two faces of the internal olefinic partner with these typical substrates. The theoretical investigation supports a concerted closed-shell mechanism and highlights the influence of the substituents on the activation parameters and on the synchronicity of C–H bond breaking and C–C bond forming during the Alder-ene step.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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{[3-(Hexadecyloxy)propoxy](hydroxy)phosphoryl}methyl 4-methylbenzenesulfonate
CAS Number:
864068-45-1
Molecular Formula:
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