Metal-Free C–C/C–N/C–C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[b]indolines

[Image: see text] A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem-bis(triflyl)ated cyclopenta[b]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence fac...

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Autores principales: Lázaro-Milla, Carlos, Yanai, Hikaru, Almendros, Pedro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8479863/
https://www.ncbi.nlm.nih.gov/pubmed/33793251
http://dx.doi.org/10.1021/acs.orglett.1c00557
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author Lázaro-Milla, Carlos
Yanai, Hikaru
Almendros, Pedro
author_facet Lázaro-Milla, Carlos
Yanai, Hikaru
Almendros, Pedro
author_sort Lázaro-Milla, Carlos
collection PubMed
description [Image: see text] A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem-bis(triflyl)ated cyclopenta[b]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence facilitated the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters. The formed cyclopenta[b]indolines can be easily transformed into a wide variety of triflylated indolines, including the tetracycle ring system found in polyveoline.
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spelling pubmed-84798632021-09-30 Metal-Free C–C/C–N/C–C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[b]indolines Lázaro-Milla, Carlos Yanai, Hikaru Almendros, Pedro Org Lett [Image: see text] A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem-bis(triflyl)ated cyclopenta[b]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence facilitated the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters. The formed cyclopenta[b]indolines can be easily transformed into a wide variety of triflylated indolines, including the tetracycle ring system found in polyveoline. American Chemical Society 2021-04-01 2021-04-16 /pmc/articles/PMC8479863/ /pubmed/33793251 http://dx.doi.org/10.1021/acs.orglett.1c00557 Text en © 2021 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Lázaro-Milla, Carlos
Yanai, Hikaru
Almendros, Pedro
Metal-Free C–C/C–N/C–C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[b]indolines
title Metal-Free C–C/C–N/C–C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[b]indolines
title_full Metal-Free C–C/C–N/C–C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[b]indolines
title_fullStr Metal-Free C–C/C–N/C–C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[b]indolines
title_full_unstemmed Metal-Free C–C/C–N/C–C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[b]indolines
title_short Metal-Free C–C/C–N/C–C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[b]indolines
title_sort metal-free c–c/c–n/c–c bond formation cascade for the synthesis of (trifluoromethyl)sulfonylated cyclopenta[b]indolines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8479863/
https://www.ncbi.nlm.nih.gov/pubmed/33793251
http://dx.doi.org/10.1021/acs.orglett.1c00557
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AT almendrospedro metalfreecccnccbondformationcascadeforthesynthesisoftrifluoromethylsulfonylatedcyclopentabindolines

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