Facile ( <i>Z</i> )‐Selective Synthesis of β,γ‐Unsaturated Ketones by a Silicon‐based Olefination Strategy

D Daniya Aynetdinova (Institute of Organic Chemistry University of Vienna Währinger Straße 38 Vienna Austria) J Jakub Brześkiewicz (Institute of Organic Chemistry University of Vienna Währinger Straße 38 Vienna Austria) N Nikolaos Skoulikas (Institute of Organic Chemistry University of Vienna Währinger Straße 38 Vienna Austria) N Nuno Maulide (Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria)

Abstract

Abstract A novel silicon‐based olefination strategy to access challenging β,γ‐( Z )‐unsaturated ketones with high diastereoselectivity in a single step from easily accessible, branched vinyl silanes is presented. This new disconnection resolves many longstanding challenges that have prevented general and efficient synthetic approaches to ( Z )‐deconjugated enones, affording a broad scope of this type of alkenes with high functional group tolerance. The developed transformation has been applied as a key step in the synthesis of a range of natural products.

Article Details

Volume / Issue Vol. 64, Issue 49
Published December 01, 2025
ISSN 1433-7851
Publisher Wiley

Journal Info

Angewandte Chemie International Edition

Wiley

ISSN: 1433-7851 Physical Sciences

Authors (4)

D

Daniya Aynetdinova

Institute of Organic Chemistry University of Vienna Währinger Straße 38 Vienna Austria

J

Jakub Brześkiewicz

Institute of Organic Chemistry University of Vienna Währinger Straße 38 Vienna Austria

N

Nikolaos Skoulikas

Institute of Organic Chemistry University of Vienna Währinger Straße 38 Vienna Austria

N

Nuno Maulide

Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria