Regioselective α-Addition of Deconjugated γ-Butenolides: Synthesis of Functionalized Dihydroquinolinones
Abstract
Abstract Regioselective reactions of γ-butenolides and the activation of an unactivated α-position represent a significant field of γ-butenolide chemistry. Compared with γ-addition, the regioselective α-addition of γ-butenolides has rarely been exploited. In this study, a regioselective Michael addition/esterification reaction of γ-butenolides with o-amino p-Quinone Methides (QMs) was generated, affording a series of functionalized dihydroquinolinones in high yields with excellent diastereoeselectivities. The studies based on density functional theory (DFT) calculations show that the observed α-regioselectivity can be attributed to steric repulsion between the base and the electrophilic o-amino p-QMs. This research is expected to provide unusual α-addition chemistry of γ-butenolides and novel synthetic methods for dihydroquinolones.
Fields of Study & Subjects
Synthesis of Indole Derivatives
Synthesis of heterocyclic compounds
Organic and Inorganic Chemical Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 11
- Pages
- 3371–3375
- Publication date
- 23 February 2026
- Language
- EN