Oxygen-to-Oxygen Silyl Migration of α‑Siloxy Sulfoxides and Oxidation-Triggered Allicin Formation

Oxidation of α-siloxy thioethers leads to the formation of the corresponding sulfoxides as unstable intermediates, which undergo an intramolecular oxygen-to-oxygen silyl migration to break the C–S linkage. This process produces silyl protected sulfenic acids and subsequently thiosulfinates. It was u...

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Bibliographic Details
Published in:Organic letters 2021-05, Vol.23 (9), p.3741-3745
Main Authors: Kelly, Shane S, Shen, Tun-Li, Xian, Ming
Format: Article
Language:English
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Summary:Oxidation of α-siloxy thioethers leads to the formation of the corresponding sulfoxides as unstable intermediates, which undergo an intramolecular oxygen-to-oxygen silyl migration to break the C–S linkage. This process produces silyl protected sulfenic acids and subsequently thiosulfinates. It was used to develop oxidation-triggered allicin donors.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01149