Enantioselective Synthesis of γ-Butyrolactones Bearing γ-Quaternary Stereocenters via Nickel-Catalyzed Reductive Coupling of Acrylates with Ketones
γ-Butyrolactones with γ-quaternary stereocenters are essential structural components in numerous natural products with significant biological activities. While chiral organocatalysis has seen considerable advancements, the development of intermolecular strategies using transition-metal catalysis has remained limited. Here, we describe a nickel-catalyzed, enantioselective reductive coupling strategy to synthesize chiral γ-butyrolactones by reacting acrylates with ketones. This method employs a chiral quinoline-oxazoline ligand and uses benzyl alcohol as a reductant, achieving high enantioselectivity under mild conditions. Additionally, preliminary mechanistic studies elucidate the reaction pathway.
Authors
- Bin Xuan (ORCID: https://orcid.org/0000-0002-4160-5693)
- Mengying Qian
- Li‐Jun Xiao (ORCID: https://orcid.org/0000-0002-3998-3628)
- Qi‐Lin Zhou (ORCID: https://orcid.org/0000-0002-4700-3765)
Institutions
- Nankai University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c02403
- Citations
- 3
- Primary Topic
- Vanadium and Halogenation Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.61