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dc.contributor.authorYasui, Motohiro
dc.contributor.authorYamada, Ayano
dc.contributor.authorTsukano, Chihiro
dc.contributor.authorHamza, Andrea
dc.contributor.authorPápai, Imre
dc.contributor.authorTakemoto, Yoshiji
dc.contributor.alternative塚野, 千尋
dc.contributor.alternative竹本, 佳司
dc.date.accessioned2020-10-16T07:39:20Z-
dc.date.available2020-10-16T07:39:20Z-
dc.date.issued2020-08-03
dc.identifier.issn1433-7851
dc.identifier.urihttp://hdl.handle.net/2433/255596-
dc.description.abstractAlthough acetalization is a fundamental transformation in organic synthesis, intermolecular asymmetric acetalization remains an unsolved problem. In this study, a thiourea‐ammonium hybrid catalyst was shown to promote the O‐alkylation of enols with a racemic γ‐chlorobutenolide through dynamic kinetic resolution to give chiral acetals with good enantioselectivity. The catalyst simultaneously activates both the nucleophile and electrophile in a multifunctional manner. This method was applied to the asymmetric synthesis of several strigolactones. DFT calculations suggest that hydrogen‐bonding interactions between the chlorine atom of the γ‐chlorobutenolide and the tosylamide hydrogen atom of the catalyst, as well as other types of noncovalent catalyst–substrate interactions, are crucial for achieving high stereoselectivity.
dc.format.mimetypeapplication/pdf
dc.language.isojpn
dc.publisherWiley
dc.rightsThis is the peer reviewed version of the following article: M. Yasui, A. Yamada, C. Tsukano, A. Hamza, I. Pápai, Y. Takemoto, Angew. Chem. Int. Ed. 2020, 59, 13479, which has been published in final form at https://doi.org/10.1002/anie.202002129. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
dc.rightsThe full-text file will be made open to the public on 3 August 2021 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
dc.rightsThis is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
dc.subjectacetalization
dc.subjectalkylation
dc.subjectasymmetric synthesis
dc.subjectorganocatalysis
dc.subjectstrigolactones
dc.titleEnantioselective Acetalization by Dynamic Kinetic Resolution for the Synthesis of γ‐Alkoxybutenolides by Thiourea/Quaternary Ammonium Salt Catalysts: Application to Strigolactones
dc.type.niitypeJournal Article
dc.identifier.jtitleAngewandte Chemie International Edition
dc.identifier.volume59
dc.identifier.issue32
dc.identifier.spage13479
dc.identifier.epage13483
dc.relation.doi10.1002/anie.202002129
dc.textversionauthor
dc.addressGraduate School of Pharmaceutical Sciences, Kyoto University
dc.addressGraduate School of Pharmaceutical Sciences, Kyoto University
dc.addressGraduate School of Pharmaceutical Sciences, Kyoto University
dc.addressInstitute of Organic Chemistry, Research Centre for Natural Sciences, Budapest
dc.addressInstitute of Organic Chemistry, Research Centre for Natural Sciences, Budapest
dc.addressGraduate School of Pharmaceutical Sciences, Kyoto University
dc.identifier.pmid32343473
dc.identifier.kakenJP17H05051 / JP18H04407 / JP16H06384
dc.relation.urlhttps://doi.org/10.1002/ange.202002129
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