The Journal of Organic Chemistry· 2026Q2
Enantioselective Synthesis of Spiropyrrolidines by Synergistic Catalysis
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- Q2SCImago
- 2026year
Short summary
A new method uses a combination of chiral phosphoric acid and palladium catalysts to create complex spiropyrrolidines with up to 99% enantiomeric excess.
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Key points
- Developed a synergistic catalysis system combining chiral phosphoric acid (CPA) and achiral palladium.
- Achieved enantioselective synthesis of spiropyrrolidines via a formal [3+2] cycloaddition.
- Obtained products in good yields (up to 83%) with high diastereoselectivities (up to 1:12 dr) and enantioselectivities (up to 99% ee).
- Methodology tolerates various substitutions on reactants and allows for further derivatization of products while retaining enantiopurity.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract A stereoselective methodology for the synthesis of highly substituted spiropyrrolidines via synergistic catalysis was developed. The transformation is based on a cooperative catalytic system combining chiral phosphoric acid (CPA) catalysis with achiral palladium catalysis and proceeds through a formal [3+2] cycloaddition of activated vinylcyclopropanes with aldimines derived from imidazolones. Under the optimized reaction conditions, a broad range of spiropyrrolidines were obtained in good combined yields (up to 83%), with high diastereoselectivities (up to 1:12 dr) and enantioselectivities reaching 99% ee. The developed methodology tolerates various substitutions on both of the reaction partners. Furthermore, selected synthetic transformations demonstrated the utility of the obtained spiropyrrolidines for further derivatization while retaining the enantiomeric purity. This work highlights the potential of synergistic CPA/transition-metal catalysis for the efficient construction of structurally complex chiral spiropyrrolidine scaffolds.
The authors' abstract, as published at the source. The Journal of Organic Chemistry, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry