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Synlett 2024; 35(04): 451-454
DOI: 10.1055/s-0041-1738454
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11th Singapore International Chemistry Conference (SICC-11)

Regioselective Ring Opening of Oxetanes Enabled by Zirconocene and Photoredox Catalysis

Kazuhiro Aida
,
Eisuke Ota  ∗
,
Junichiro Yamaguchi  ∗
This work was supported by JSPS KAKENHI Grants Nos. JP21H05213 (Digi-TOS) (to J.Y.) and JP20K15290 (to E.O.), the Sumitomo Foundation (to E.O.), the Satomi Foundation (to E.O.), and Daiichi Kigenso Kagaku Kogyo (to E.O.). This work was also partly supported by JST ERATO Grant No. JPMJER1901 (to J.Y.).
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Abstract

Oxetanes are frequently utilized in organic synthesis, both as target products and as fairly reactive intermediates. Whereas ring cleavage of oxetanes through polar mechanisms has been extensively investigated, their radical-based counterparts remain underexplored. We used zirconocene and photoredox catalysis to open an oxetane ring in a radical manner. In our protocol, the reaction selectively delivers the more-substituted alcohols via putative less-stable radicals. This method not only affords the corresponding hydrogenated products, but also provides unique benzylidene acetal products.

Key words

zirconocene - photoredox catalysis - oxetanes - reverse regioselectivity - C–O bond homolysis - radicals

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738454.
  • Supporting Information


Publication History

Received: 01 July 2023

Accepted after revision: 14 August 2023

Article published online:
27 October 2023

© 2023. Thieme. All rights reserved

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