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Article: Highly Enantioselective Iron-​Catalyzed cis-​Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an FeIII-​OOH Reactive Intermediate

TitleHighly Enantioselective Iron-​Catalyzed cis-​Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an FeIII-​OOH Reactive Intermediate
Authors
Issue Date2016
PublisherWiley-VCH Verlag GmbH & Co. KGaA.
Citation
Angewandte Chemie, International Edition, 2016, v. 55, p. 10253-10257 How to Cite?
AbstractThe development of environmentally benign catalysts for highly enantioselective asymmetric cis-dihydroxylation (AD) of alkenes with broad substrate scope remains a challenge. By employing [FeII(L)(OTf)2] (L = N,N’-dimethyl-N,N’-bis(2-methyl-8-quinolyl)-cyclohexane-1,2-diamine) as a catalyst, cis-diols in up to 99.8% ee with 85% isolated yield have been achieved in AD of alkenes with H2O2 as an oxidant and alkenes in a limiting amount. This “[FeII(L)(OTf)2] + H2O2” method is applicable to both (E)-alkenes and terminal alkenes (24 examples > 80% ee, up to 1 g scale). Mechanistic studies, including 18O-labeling, UV/Vis, EPR, ESI-MS analyses, and DFT calculations lend evidence for the involvement of chiral FeIII-OOH active species in enantioselective formation of the two C=O bonds.
Persistent Identifierhttp://hdl.handle.net/10722/234030

 

DC FieldValueLanguage
dc.contributor.authorZang, C-
dc.contributor.authorLiu, Y-
dc.contributor.authorXu, ZJ-
dc.contributor.authorTSE, CW-
dc.contributor.authorGuan, X-
dc.contributor.authorWEI, J-
dc.contributor.authorHuang, JS-
dc.contributor.authorChe, CM-
dc.date.accessioned2016-10-14T06:58:35Z-
dc.date.available2016-10-14T06:58:35Z-
dc.date.issued2016-
dc.identifier.citation Angewandte Chemie, International Edition, 2016, v. 55, p. 10253-10257-
dc.identifier.urihttp://hdl.handle.net/10722/234030-
dc.description.abstractThe development of environmentally benign catalysts for highly enantioselective asymmetric cis-dihydroxylation (AD) of alkenes with broad substrate scope remains a challenge. By employing [FeII(L)(OTf)2] (L = N,N’-dimethyl-N,N’-bis(2-methyl-8-quinolyl)-cyclohexane-1,2-diamine) as a catalyst, cis-diols in up to 99.8% ee with 85% isolated yield have been achieved in AD of alkenes with H2O2 as an oxidant and alkenes in a limiting amount. This “[FeII(L)(OTf)2] + H2O2” method is applicable to both (E)-alkenes and terminal alkenes (24 examples > 80% ee, up to 1 g scale). Mechanistic studies, including 18O-labeling, UV/Vis, EPR, ESI-MS analyses, and DFT calculations lend evidence for the involvement of chiral FeIII-OOH active species in enantioselective formation of the two C=O bonds.-
dc.languageeng-
dc.publisherWiley-VCH Verlag GmbH & Co. KGaA. -
dc.relation.ispartof Angewandte Chemie, International Edition-
dc.rightspostprint: This is the accepted version of the following article: FULL CITE, which has been published in final form at [Link to final article]. Preprint This is the pre-peer reviewed version of the following article: FULL CITE, which has been published in final form at [Link to final article].-
dc.titleHighly Enantioselective Iron-​Catalyzed cis-​Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an FeIII-​OOH Reactive Intermediate-
dc.typeArticle-
dc.identifier.emailLiu, Y: lyg100@hku.hk-
dc.identifier.emailGuan, X: xgguan@hku.hk-
dc.identifier.emailHuang, JS: jshuang@hku.hk-
dc.identifier.emailChe, CM: chemhead@hku.hk-
dc.identifier.authorityLiu, Y=rp00749-
dc.identifier.authorityHuang, JS=rp00709-
dc.identifier.authorityChe, CM=rp00670-
dc.identifier.doi10.1002/anie.201603410-
dc.identifier.hkuros267785-
dc.identifier.volume55-
dc.identifier.spage10253-
dc.identifier.epage10257-
dc.publisher.placeWeinheim, Germany-

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