Related Experiment Video
Updated: Feb 24, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
A Copper(I)-Catalyzed Addition/Annulation Sequence for the Two-Component Synthesis of γ-Ylidenebutenolides
Sangwon Seo1, Michael C Willis1
1Department of Chemistry, University of Oxford, Chemistry Research Laboratory , Mansfield Road, Oxford, OX1 3TA, U.K.
Abstract:
A highly efficient Cu(I)-catalyzed addition/annulation sequence has been developed for the synthesis of (Z)-ylidenebutenolides employing readily available α-ketoacids and alkynes as substrates. The reactions employ a simple commercially available Cu(I)-catalyst, display good substrate scope, and deliver products with high stereoselectivity. The synthetic utility of the method is demonstrated by the straightforward derivatization of the ylidenebutenolides into a diverse range of heterocycles, and also by the preparation of the natural product bovolide, and analogs thereof.
Related Concept Videos
Cycloaddition Reactions: Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

