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C7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptamines

dc.contributor.authorLoach, Richard Peter
dc.contributor.authorFenton, Owen S.
dc.contributor.authorAmaike, Kazuma
dc.contributor.authorSiegel, Dustin Scott
dc.contributor.authorOzkal, Erhan
dc.contributor.authorMovassaghi, Mohammad
dc.date.accessioned2017-06-09T19:58:33Z
dc.date.available2017-06-09T19:58:33Z
dc.date.issued2014-10
dc.date.submitted2014-09
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttp://hdl.handle.net/1721.1/109780
dc.description.abstractA versatile strategy for C7-selective boronation of tryptophans, tryptamines, and 3-alkylindoles by way of a single-pot C2/C7-diboronation–C2-protodeboronation sequence is described. The combination of a mild iridium-catalyzed C2/C7-diboronation followed by an in situ palladium-catalyzed C2-protodeboronation allows efficient entry to valuable C7-boroindoles that enable further C7-derivatization. The versatility of the chemistry is highlighted by the gram-scale synthesis of C7-boronated N-Boc-L-tryptophan methyl ester and the rapid synthesis of C7-halo, C7-hydroxy, and C7-aryl tryptophan derivatives.en_US
dc.description.sponsorshipNational Institute of General Medical Sciences (U.S.) (GM089732)en_US
dc.description.sponsorshipNational Institute of General Medical Sciences (U.S.) (GM074825)en_US
dc.description.sponsorshipNational Science Foundation (U.S.) (CHE-1205646)en_US
dc.language.isoen_US
dc.publisherAmerican Chemical Society (ACS)en_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/jo502062zen_US
dc.rightsArticle is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.en_US
dc.sourceACSen_US
dc.titleC7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptaminesen_US
dc.typeArticleen_US
dc.identifier.citationLoach, Richard P.; Fenton, Owen S.; Amaike, Kazuma; Siegel, Dustin S.; Ozkal, Erhan and Movassaghi, Mohammad. "C7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptamines." 79, no. 22 (November 2014): 11254–11263 © 2014 American Chemical Societyen_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.contributor.mitauthorLoach, Richard Peter
dc.contributor.mitauthorFenton, Owen S.
dc.contributor.mitauthorAmaike, Kazuma
dc.contributor.mitauthorSiegel, Dustin Scott
dc.contributor.mitauthorOzkal, Erhan
dc.contributor.mitauthorMovassaghi, Mohammad
dc.relation.journalJournal of Organic Chemistryen_US
dc.eprint.versionFinal published versionen_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/PeerRevieweden_US
dspace.orderedauthorsLoach, Richard P.; Fenton, Owen S.; Amaike, Kazuma; Siegel, Dustin S.; Ozkal, Erhan; Movassaghi, Mohammaden_US
dspace.embargo.termsNen_US
dc.identifier.orcidhttps://orcid.org/0000-0002-4426-7474
dc.identifier.orcidhttps://orcid.org/0000-0002-5585-9280
dc.identifier.orcidhttps://orcid.org/0000-0003-3080-1063
mit.licensePUBLISHER_POLICYen_US


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