“Amphiphilic” Cleavage of γ-Stannyl Ketones with ATPH/RLi: Application to Enone Fragmentation by the Conjugate Addition – Cleavage Sequence

Autor: Kondo, Yuichiro, Kon-i, Kana, Iwasaki, Atsuko, Ooi, Takashi
Zdroj: Angewandte Chemie. International Edition; January 17, 2000, Vol. 39 Issue: 2 p414-416, 3p
Abstrakt: The use of a combined Lewis acid/base system consisting of aluminum tris(2,6-diphenylphenoxide) (ATPH) and MeLi has allowed the electrophilically activated nucleophilic (“amphiphilic”) cleavage of Cα−Cβ bonds in γ-stannyl ketones. Through combination with the conjugate addition of α-stannyl carbanion to enone, this approach constitutes a novel two-step conjugate addition – cleavage sequence that leads to functionalized ketones (see reaction).
Databáze: Supplemental Index