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Synthesis 2024; 56(02): 275-280
DOI: 10.1055/a-2182-9098
paper

Lewis Acid Catalyzed 4π-Electrocyclization of Donor–Acceptor Stenhouse Adducts

Seung Hyeon Yoon
a   Department of Applied Biology and Chemistry, Seoul National University, Seoul, 08826, Republic of Korea
,
Kye Sung Park
b   Department of Agricultural Biotechnology, Seoul National University, Seoul, 08826, Republic of Korea
,
Jaehee Kim
b   Department of Agricultural Biotechnology, Seoul National University, Seoul, 08826, Republic of Korea
,
Yonghoon Kwon∗
a   Department of Applied Biology and Chemistry, Seoul National University, Seoul, 08826, Republic of Korea
b   Department of Agricultural Biotechnology, Seoul National University, Seoul, 08826, Republic of Korea
› InstitutsangabenThis work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (No. RS-2023-00207820).
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Abstract

Lewis acid catalyzed 4π-electrocyclization of Donor–Acceptor Stenhouse Adducts (DASAs) has been developed. By employing catalytic quantities of Dy(OTf)3, a highly efficient transformation of acyclic DASAs into the corresponding cyclized isomers was achieved. Notably, this transformation exhibited exceptional yields, particularly in the case of first generation DASAs. In addition, Lewis acid catalysis enabled one-pot synthesis of the cyclopentenone product from the ‘donor’ and ‘acceptor’ components.

Key words

Dy(OTf)3 - furfural - secondary amine - photoswitch

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2182-9098.
  • Supporting Information


Publikationsverlauf

Eingereicht: 11. September 2023

Angenommen nach Revision: 27. September 2023

Accepted Manuscript online:
27. September 2023

Artikel online veröffentlicht:
30. Oktober 2023

© 2023. Thieme. All rights reserved

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