β‐Functionalized and α,β‐Difunctionalized Ketones from 1‐Arylallylic Alcohols via Dipotassio α,β‐Dianion Intermediates

This study reports the synthesis of diverse β‐functionalized ketones from readily available 1‐arylallylic alcohols in the presence of (trimethylsilyl)methylpotassium (TMSCH2K). The reaction proceeded via the formation of the highly nucleophilic dipotassio α,β‐dianion as the key intermediate, which s...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Advanced synthesis & catalysis 2023-03, Vol.365 (6), p.826-833
Hauptverfasser: Hayashi, Rikuo, Ando, Kaori, Udagawa, Taro, Sai, Masahiro
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:This study reports the synthesis of diverse β‐functionalized ketones from readily available 1‐arylallylic alcohols in the presence of (trimethylsilyl)methylpotassium (TMSCH2K). The reaction proceeded via the formation of the highly nucleophilic dipotassio α,β‐dianion as the key intermediate, which served as a metal homoenolate equivalent. This protocol also allowed the one‐pot synthesis of α,β‐difunctionalized ketones using two different electrophiles, thus demonstrating its synthetic advantages over other protocols involving metal homoenolates.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202201047