Tandem homologation-acylation chemistry: Single and double homologation. (2nd July 2021)

• Record Type: Journal Article
• Authors: Henderson, Carley S.; Mazzone, Jennifer R.; Moore, Amanda M.; Zercher, Charles K.
• Is Part Of: Tetrahedron. Volume 91(2021)
• Publication Date: 2021-07-02
• Subjects: Zinc carbenoid -- Homologation -- Acylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132223
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Treatment of β-dicarbonyls with the Furakawa-variant of the Simmons-Smith reagent results in homologation and production of an intermediate zinc enolate. Treatment of the enolate with various acylating agents generate products with both γ-dicarbonyl functionality and β−dicarbonyl functionality. In situ exposure of the acylated product to additional zinc carbenoid effects a second regiospecific homologation reaction. Graphical abstract: Image 1