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Updated: Feb 24, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Regioselective α-Addition of Deconjugated γ-Butenolides: Synthesis of Functionalized Dihydroquinolinones
Changhong Han1, Hongli Wu2, Tao Liu1
1Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.
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.
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