Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/137753
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dc.contributor.authorZheng, Pengchengen_US
dc.contributor.authorWu, Shuquanen_US
dc.contributor.authorMou, Chenglien_US
dc.contributor.authorXue, Weien_US
dc.contributor.authorJin, Zhichaoen_US
dc.contributor.authorChi, Robin Yongguien_US
dc.date.accessioned2020-04-13T07:38:04Z-
dc.date.available2020-04-13T07:38:04Z-
dc.date.issued2019-
dc.identifier.citationZheng, P., Wu, S., Mou, C., Jin, Z., & Chi, R. Y. (2019). Addition of a carbene catalyst to indole aryl aldehyde activates a remote δ-sp2 carbon for protonation and formal [4+2] reaction. Organic Letters, 21(13), 5026-5029. doi:10.1021/acs.orglett.9b01624en_US
dc.identifier.issn1523-7060en_US
dc.identifier.urihttps://hdl.handle.net/10356/137753-
dc.description.abstractThe addition of a carbene catalyst to an indole aryl aldehyde leads to the activation of a remote sp2 carbon that is five atoms away from the catalyst. The unsaturated Breslow intermediate formed between the catalyst and substrate undergoes an internal redox reaction and remote carbon protonation to generate an analogous azolium vinyl enolate intermediate. Subsequent [4+2] reaction with cyclic imine substrates eventually affords multicyclic pyridoindoles as nearly single diastereomers with excellent enantioselectivities.en_US
dc.description.sponsorshipNRF (Natl Research Foundation, S’pore)en_US
dc.description.sponsorshipASTAR (Agency for Sci., Tech. and Research, S’pore)en_US
dc.description.sponsorshipMOE (Min. of Education, S’pore)en_US
dc.language.isoenen_US
dc.relation.ispartofOrganic Lettersen_US
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b01624en_US
dc.subjectScience::Chemistry::Organic chemistryen_US
dc.titleAddition of a carbene catalyst to indole aryl aldehyde activates a remote δ-sp2 carbon for protonation and formal [4+2] reactionen_US
dc.typeJournal Articleen
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.identifier.doi10.1021/acs.orglett.9b01624-
dc.description.versionAccepted versionen_US
dc.identifier.pmid31199655-
dc.identifier.scopus2-s2.0-85067946714-
dc.identifier.issue13en_US
dc.identifier.volume21en_US
dc.identifier.spage5026en_US
dc.identifier.epage5029en_US
dc.subject.keywordsCarbene Catalysten_US
dc.subject.keywordsBreslow Intermediateen_US
item.grantfulltextopen-
item.fulltextWith Fulltext-
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