File Download
  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Chiral cis-iron(ii) complexes with metal- and ligand-centered chirality for highly regio- and enantioselective alkylation of N-heteroaromatics

TitleChiral cis-iron(ii) complexes with metal- and ligand-centered chirality for highly regio- and enantioselective alkylation of N-heteroaromatics
Authors
KeywordsAlkylation
Aniline
Chirality
Enantioselectivity
Ligands
Issue Date2020
PublisherRoyal Society of Chemistry: Open Access. The Journal's web site is located at http://www.rsc.org/publishing/journals/sc/About.asp
Citation
Chemical Science, 2020, v. 11 n. 3, p. 684-693 How to Cite?
AbstractIron-catalyzed highly regio- and enantioselective organic transformations with generality and broad substrate scope have profound applications in modern synthetic chemistry; an example is herein described based on cis-FeII complexes having metal- and ligand-centered chirality. The cis-β FeII(N4) complex [FeII(L)(OTf)2] (L = N,N′-bis(2,3-dihydro-1H-cyclopenta-[b]quinoline-5-yl)-N,N′-dimethylcyclohexane-1,2-diamine) is an effective chiral catalyst for highly regio- and enantioselective alkylation of N-heteroaromatics with α,β-unsaturated 2-acyl imidazoles, including asymmetric N1, C2, C3 alkylations of a broad range of indoles (34 examples) and alkylation of pyrroles and anilines (14 examples), all with high product yields (up to 98%), high enantioselectivity (up to >99% ee) and high regioselectivity. DFT calculations revealed that the “chiral-at-metal” cis-β configuration of the iron complex and a secondary π–π interaction are responsible for the high enantioselectivity.
Persistent Identifierhttp://hdl.handle.net/10722/282888
ISSN
2023 Impact Factor: 7.6
2023 SCImago Journal Rankings: 2.333
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorWei, J-
dc.contributor.authorCao, B-
dc.contributor.authorTse, CW-
dc.contributor.authorChang, XY-
dc.contributor.authorZhou, CY-
dc.contributor.authorChe, CM-
dc.date.accessioned2020-06-05T06:22:44Z-
dc.date.available2020-06-05T06:22:44Z-
dc.date.issued2020-
dc.identifier.citationChemical Science, 2020, v. 11 n. 3, p. 684-693-
dc.identifier.issn2041-6520-
dc.identifier.urihttp://hdl.handle.net/10722/282888-
dc.description.abstractIron-catalyzed highly regio- and enantioselective organic transformations with generality and broad substrate scope have profound applications in modern synthetic chemistry; an example is herein described based on cis-FeII complexes having metal- and ligand-centered chirality. The cis-β FeII(N4) complex [FeII(L)(OTf)2] (L = N,N′-bis(2,3-dihydro-1H-cyclopenta-[b]quinoline-5-yl)-N,N′-dimethylcyclohexane-1,2-diamine) is an effective chiral catalyst for highly regio- and enantioselective alkylation of N-heteroaromatics with α,β-unsaturated 2-acyl imidazoles, including asymmetric N1, C2, C3 alkylations of a broad range of indoles (34 examples) and alkylation of pyrroles and anilines (14 examples), all with high product yields (up to 98%), high enantioselectivity (up to >99% ee) and high regioselectivity. DFT calculations revealed that the “chiral-at-metal” cis-β configuration of the iron complex and a secondary π–π interaction are responsible for the high enantioselectivity.-
dc.languageeng-
dc.publisherRoyal Society of Chemistry: Open Access. The Journal's web site is located at http://www.rsc.org/publishing/journals/sc/About.asp-
dc.relation.ispartofChemical Science-
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.-
dc.subjectAlkylation-
dc.subjectAniline-
dc.subjectChirality-
dc.subjectEnantioselectivity-
dc.subjectLigands-
dc.titleChiral cis-iron(ii) complexes with metal- and ligand-centered chirality for highly regio- and enantioselective alkylation of N-heteroaromatics-
dc.typeArticle-
dc.identifier.emailWei, J: weijh@connect.hku.hk-
dc.identifier.emailCao, B: bcao@hku.hk-
dc.identifier.emailZhou, CY: cyzhou@hku.hk-
dc.identifier.emailChe, CM: chemhead@hku.hk-
dc.identifier.authorityZhou, CY=rp00843-
dc.identifier.authorityChe, CM=rp00670-
dc.description.naturepublished_or_final_version-
dc.identifier.doi10.1039/C9SC04858H-
dc.identifier.scopuseid_2-s2.0-85078443214-
dc.identifier.hkuros310315-
dc.identifier.volume11-
dc.identifier.issue3-
dc.identifier.spage684-
dc.identifier.epage693-
dc.identifier.isiWOS:000508917000004-
dc.publisher.placeUnited Kingdom-
dc.identifier.issnl2041-6520-

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats