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Title: Enantioselective Acetalization by Dynamic Kinetic Resolution for the Synthesis of γ‐Alkoxybutenolides by Thiourea/Quaternary Ammonium Salt Catalysts: Application to Strigolactones
Authors: Yasui, Motohiro
Yamada, Ayano
Tsukano, Chihiro  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-9361-0857 (unconfirmed)
Hamza, Andrea
Pápai, Imre
Takemoto, Yoshiji  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0003-1375-3821 (unconfirmed)
Author's alias: 塚野, 千尋
竹本, 佳司
Keywords: acetalization
alkylation
asymmetric synthesis
organocatalysis
strigolactones
Issue Date: 3-Aug-2020
Publisher: Wiley
Journal title: Angewandte Chemie International Edition
Volume: 59
Issue: 32
Start page: 13479
End page: 13483
Abstract: Although 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.
Rights: This 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.
The 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'.
This 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。
URI: http://hdl.handle.net/2433/255596
DOI(Published Version): 10.1002/anie.202002129
PubMed ID: 32343473
Related Link: https://doi.org/10.1002/ange.202002129
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