Direct Synthesis of β,γ‐Disubstituted Butenolides via Regioselective β‐Addition of Deconjugated Butenolides to Donor–Acceptor Cyclopropanes Under Lewis Acid Catalysis
Abstract
ABSTRACT We report the first Lewis acid catalyzed β‐selective nucleophilic addition of β,γ‐unsaturated‐γ‐butenolides to donor–acceptor cyclopropanes (DACs). The transformation proceeds smoothly under mild conditions to afford β,γ‐disubstituted butenolide derivatives in moderate to high yields, demonstrating an enol‐ester‐type reactivity of lactone. The reaction displays excellent regioselectivity, thereby expanding the reactivity of deconjugated butenolides beyond conventional α‐ and γ‐functionalization. The reaction was successfully scaled up to the gram scale.
Fields of Study & Subjects
Cyclopropane Reaction Mechanisms
Organic Chemistry Synthesis Methods
Asymmetric Synthesis and Catalysis
Publication details
- Journal / source
- Asian Journal of Organic Chemistry
- Volume
- 15
- Issue
- 1
- Publication date
- 1 January 2026
- Language
- EN