Reductive Cleavage of Propargylic Ethers with Alkali Metal: Application to the Synthesis of Allenylboronates

Reductive Cleavage of Propargylic Ethers with Alkali Metal: Application to the Synthesis of Allenylboronates

Treatment of propargylic ethers with sodium dispersion in the presence of lithium iodide results in the generation of the corresponding carbanion species via cleavage of the propargylic C–O bond. The anionic species react with trimethoxyborane to yield the allenylboronates including highly substitut...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2021-11, Vol.23 (21), p.8590-8594
Hauptverfasser: Koyama, Shunsuke, Takahashi, Fumiya, Saito, Hayate, Yorimitsu, Hideki
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Treatment of propargylic ethers with sodium dispersion in the presence of lithium iodide results in the generation of the corresponding carbanion species via cleavage of the propargylic C–O bond. The anionic species react with trimethoxyborane to yield the allenylboronates including highly substituted ones that are difficult to synthesize.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03316